Product Name

  • Name

    (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid

  • EINECS
  • CAS No. 364750-80-1
  • Article Data8
  • CAS DataBase
  • Density 1.150
  • Solubility
  • Melting Point
  • Formula C11H19 N O4
  • Boiling Point 343 ºC
  • Molecular Weight 229.276
  • Flash Point 161 ºC
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 364750-80-1 ((2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid)
  • Hazard Symbols
  • Synonyms (2S,4R)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid; (2S,4R)-4-Methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester
  • PSA 66.84000
  • LogP 1.65440

Synthetic route

tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate
220047-75-6

tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 15h;100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; NaH2PO4 buffer; sodium hypochlorite In water; acetonitrile at 45℃; for 24h; pH=6.6;84%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In acetone at 0℃; for 2h;
C11H19NO4

C11H19NO4

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: C11H19NO4 With trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran; toluene at -30 - 23℃; for 0.666667h; Inert atmosphere;
Stage #2: With methanesulfonyl chloride; triethylamine In tetrahydrofuran at -78 - 23℃; for 1h; Inert atmosphere; Further stages;		44%
L-leucine
61-90-5

L-leucine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

A

N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline
364750-81-2

N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline

B

(2S)-2-(ter-butoxycarbonylamino)-4,4-dimethyl-4-butanolide

(2S)-2-(ter-butoxycarbonylamino)-4,4-dimethyl-4-butanolide

C

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multistep reaction;A n/a
B 12%
C n/a
...Expand
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h
2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C
3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
4.1: 78 percent / TEA; DMAP / CH2Cl2
5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
7.1: Raney-Ni; hydrogen / methanol / Heating
8.1: TBAF / tetrahydrofuran
9.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: lithium borohydride / tetrahydrofuran / 20 °C
View Scheme
tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate
61478-26-0

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 78 percent / TEA; DMAP / CH2Cl2
2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
4.1: Raney-Ni; hydrogen / methanol / Heating
5.1: TBAF / tetrahydrofuran
6.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C
2.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
3.1: 78 percent / TEA; DMAP / CH2Cl2
4.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
5.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
6.1: Raney-Ni; hydrogen / methanol / Heating
7.1: TBAF / tetrahydrofuran
8.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
125653-58-9

(2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
3.1: Raney-Ni; hydrogen / methanol / Heating
4.1: TBAF / tetrahydrofuran
5.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(2S,4R)-4-Hydroxy-2-isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-Hydroxy-2-isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
2.1: 78 percent / TEA; DMAP / CH2Cl2
3.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
5.1: Raney-Ni; hydrogen / methanol / Heating
6.1: TBAF / tetrahydrofuran
7.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h
2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C
3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
4.1: 78 percent / TEA; DMAP / CH2Cl2
5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
7.1: Raney-Ni; hydrogen / methanol / Heating
8.1: TBAF / tetrahydrofuran
9.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(S)-tert-butyl 2-(hydroxymethyl)-4-methylenepyrrolidine-1-carboxylate
181295-78-3

(S)-tert-butyl 2-(hydroxymethyl)-4-methylenepyrrolidine-1-carboxylate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr
2: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TBAF / tetrahydrofuran
2: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate
220993-22-6

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
1.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
2.1: Raney-Ni; hydrogen / methanol / Heating
3.1: TBAF / tetrahydrofuran
4.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
Multi-step reaction with 5 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C
2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,4-dioxane; water / 1 h / 100 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C
4: hydrogen; Crabtree's catalyst / dichloromethane / 12 h / 20 °C
5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 15 h / 20 °C
View Scheme
(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylenepyrrolidine
540501-23-3

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylenepyrrolidine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / TBAF / tetrahydrofuran / 6 h / 20 °C
2: 90 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr
3: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine
540501-65-3

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Raney-Ni; hydrogen / methanol / Heating
2: TBAF / tetrahydrofuran
3: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme
(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-methylpyrrolidine
220047-73-4

(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-methylpyrrolidine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
2: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine
220047-57-4

((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 63 percent / K2CO3 / dimethylformamide / 48 h / 80 °C
2: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / pyridine / 24 h / 0 °C
4: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
5: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C
6: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
7: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
8: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
9: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
10: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
11: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1: 90 percent / NaBH3CN / 1,2-dichloro-ethane / 6 h / Ambient temperature
2: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / pyridine / 24 h / 0 °C
4: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
5: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C
6: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
7: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
8: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
9: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
10: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
11: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
(2S,4R)-2-Benzyloxymethyl-4-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
220047-71-2

(2S,4R)-2-Benzyloxymethyl-4-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
2: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
3: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-hydroxymethylpyrrolidine
212266-65-4

(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-hydroxymethylpyrrolidine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
2: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
3: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
4: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
((3R,4S,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol
220047-66-5

((3R,4S,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
2: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
3: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
4: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
5: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
6: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-oxiranylmethyl-amine

((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-oxiranylmethyl-amine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C
2: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
3: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
4: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
5: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
6: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
7: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
220047-69-8

(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
2: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
3: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
4: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
5: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
(S)-3-[((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-propane-1,2-diol
212266-69-8

(S)-3-[((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-propane-1,2-diol

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 85 percent / pyridine / 24 h / 0 °C
2: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
3: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C
4: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
5: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
6: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
7: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
8: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
9: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine
212266-68-7

((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / pyridine / 24 h / 0 °C
3: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
4: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C
5: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
6: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
7: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
8: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
9: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
10: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
Toluene-4-sulfonic acid (S)-3-[((R)-2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-2-hydroxy-propyl ester
212266-70-1

Toluene-4-sulfonic acid (S)-3-[((R)-2-benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-2-hydroxy-propyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 99 percent / K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
2: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C
3: 95 percent / H2 / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature
4: 100 percent / Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
5: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h
6: 87 percent / NaBH4 / dimethylsulfoxide / 16 h / 45 °C
7: 92 percent / H2 / Pd/C / methanol / 18 h / 760 Torr / Ambient temperature
8: aq. NaHCO3, NaOCl, KBr, TEMPO / acetone / 2 h / 0 °C
View Scheme
4-methyl-pyrrolidine-2-carboxylic acid methyl ester

4-methyl-pyrrolidine-2-carboxylic acid methyl ester

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C
2: palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr
3: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C
View Scheme
C20H34N2O4Si
1353864-31-9

C20H34N2O4Si

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: [bis(acetoxy)iodo]benzene; palladium diacetate; acetic acid / toluene / 24 h / 110 °C / Inert atmosphere
2: hydrogenchloride; water / 1,4-dioxane / 24 h / 20 °C
3: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C
4: palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr
5: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C
View Scheme
C20H32N2O4Si
1353864-33-1

C20H32N2O4Si

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride; water / 1,4-dioxane / 24 h / 20 °C
2: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C
3: palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr
4: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C
View Scheme
C15H19NO4
1353864-35-3

C15H19NO4

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr
2: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C
View Scheme
methyl (L)-leucinate hydrochloride
7517-19-3

methyl (L)-leucinate hydrochloride

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
2: [bis(acetoxy)iodo]benzene; palladium diacetate; acetic acid / toluene / 24 h / 110 °C / Inert atmosphere
3: hydrogenchloride; water / 1,4-dioxane / 24 h / 20 °C
4: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C
5: palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr
6: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C
View Scheme
1-tert-butyl 2-methyl (2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate
138512-74-0

1-tert-butyl 2-methyl (2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 14h;
With water; lithium hydroxide In ethanol at 0 - 20℃; for 5h;
With lithium borohydride In tetrahydrofuran at 20℃;92 g
2-oxo-2-phenylethyl ((benzyloxy)carbonyl)-L-allothreoninate
1542206-68-7

2-oxo-2-phenylethyl ((benzyloxy)carbonyl)-L-allothreoninate

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

2-((2S,3S)-3-(((benzyloxy)carbonyl)amino)-4-oxo-4-(2-oxo-2-phenylethoxy)butan-2-yl) 1-(tert-butyl) (2S,4S)-4-methylpyrrolidine-1,2-dicarboxylate

2-((2S,3S)-3-(((benzyloxy)carbonyl)amino)-4-oxo-4-(2-oxo-2-phenylethoxy)butan-2-yl) 1-(tert-butyl) (2S,4S)-4-methylpyrrolidine-1,2-dicarboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;83%
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate
220047-75-6

tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 0 - 30℃; for 2h;83%
methanol
67-56-1

methanol

<2-(13)C>acetyl chloride
14770-40-2

<2-(13)C>acetyl chloride

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

N-(2-13CH3-acetyl)-(2S,4R)-4-methylproline methyl ester

N-(2-13CH3-acetyl)-(2S,4R)-4-methylproline methyl ester

Conditions
ConditionsYield
Stage #1: methanol; (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid With acetyl chloride at 0 - 20℃;
Stage #2: <2-(13)C>acetyl chloride With dmap In dichloromethane at 20℃; for 24h;		77%
...Expand
4-Bromo-benzene-1,2-diamine
1575-37-7

4-Bromo-benzene-1,2-diamine

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

C17H22BrN3O2

C17H22BrN3O2

Conditions
ConditionsYield
Stage #1: (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: 4-Bromo-benzene-1,2-diamine In tetrahydrofuran at 20℃; for 2h;		72%
diazomethane
186581-53-3, 908094-01-9

diazomethane

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

1-tert-butyl 2-methyl (2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate
138512-74-0

1-tert-butyl 2-methyl (2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate

Conditions
ConditionsYield
In diethyl ether Yield given;
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

trans-4-methyl-L-proline
23009-50-9

trans-4-methyl-L-proline

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 1.5h;
Multi-step reaction with 2 steps
1: diethyl ether
2: 1.) aq. HCl, 2.) propylene oxide / 1.) 100 deg C, 3 h, 2.) EtOH, heating
View Scheme
methanol
67-56-1

methanol

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

(2S,4R)-4-Methyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride

(2S,4R)-4-Methyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride

Conditions
ConditionsYield
With acetyl chloride at 0 - 20℃; for 6h;
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

trans-4-methyl-L-proline hydrochloride

trans-4-methyl-L-proline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 1.5h;
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine
901139-04-6

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aq. HCl / dioxane / 1.5 h
2: 1.11 g / aq. NaHCO3 / dioxane / 27 h
3: 442 mg / PyBroP; DIEA / CH2Cl2 / 36 h / 20 °C
4: 84 percent / H2 / Pd/C / methanol / 5 h
View Scheme
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
901139-69-3

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aq. HCl / dioxane / 1.5 h
2: 1.11 g / aq. NaHCO3 / dioxane / 27 h
3: 520 mg / DIEA; PyBroP / CH2Cl2 / 40 h / 20 °C
4: 66 percent / hydrogen / Pd/C / methanol / 2.5 h
View Scheme
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine benzyl ester
901138-97-4

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HCl / dioxane / 1.5 h
2: 1.11 g / aq. NaHCO3 / dioxane / 27 h
3: 442 mg / PyBroP; DIEA / CH2Cl2 / 36 h / 20 °C
View Scheme
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
901139-63-7

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HCl / dioxane / 1.5 h
2: 1.11 g / aq. NaHCO3 / dioxane / 27 h
3: 520 mg / DIEA; PyBroP / CH2Cl2 / 40 h / 20 °C
View Scheme
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid
364750-80-1

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid
333777-34-7

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl / dioxane / 1.5 h
2: 1.11 g / aq. NaHCO3 / dioxane / 27 h
View Scheme

(2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid Chemical Properties

Product Name: (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid 
Molecular Structure of (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid (CAS NO.364750-80-1):

Molecular Formula: C11H19NO4
Molecular Weight: 229.2729
Synonyms of (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid (CAS NO.364750-80-1): (2S,4R)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid ; (2S,4R)-4-Methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester
CAS NO: 364750-80-1 
Index of Refraction: 1.491
Molar Refractivity: 57.644 cm3
Molar Volume: 199.2 cm3
Surface Tension: 42.049 dyne/cm
Density: 1.151 g/cm3
Flash Point: 161.361 °C
Enthalpy of Vaporization: 64.509 kJ/mol
Boiling Point of (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid (CAS NO.364750-80-1): 343.199 °C at 760 mmHg

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