L-Proline, 3-hydroxy-,(3S)- supplier

Name
L-Proline, 3-hydroxy-,(3S)-
EINECS
CAS No. 4298-08-2
Article Data34
CAS DataBase
Density 1.395g/cm³
Solubility
Melting Point 235oC
Formula C₅H₉NO₃
Boiling Point 355.233 °C at 760 mmHg
Molecular Weight 131.131
Flash Point 168.639 °C
Transport Information
Appearance White to light beige powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms L-Proline,3-hydroxy-, trans-;Proline, 3-hydroxy-, L-trans- (8CI);(2S,3S)-(-)-3-Hydroxy-L-proline;(2S,3S)-3-Hydroxyproline;trans-3-Hydroxy-L-proline;trans-3-Hydroxyproline;
PSA 69.56000
LogP -0.87740

Synthetic route

: 312583-31-6
(2S,3S)-N-benzyl-2-hydroxyproline

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 13h;	98%

: (S,S)-2-(tert-butoxycarbonyl)-3-acetoxypyrrolidine

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h;	89%

: (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water Ambient temperature;	88%

: 120789-99-3
Potassium; (2S,3S)-2-amino-3-hydroxy-5,5-dimethoxy-pentanoate

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With hydrogen; trifluoroacetic acid; platinum(IV) oxide In ethanol; water for 15h; Ambient temperature;	87%

: (S,S)-N-(1)-(tert-butoxycarbonyl)-2-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h;	87%

: 156045-82-8
(2S,3S)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 3h; Inert atmosphere; Reflux;	80%
With hydrogenchloride for 3h; Heating;	70%

: FR901469 hydrochloride

A: 6208-98-6
threo-β-hydroxy-L-glutamic acid (threo-L-BHGA)

B: 928-17-6, 2398-34-7, 83780-74-9, 20595-04-4
(R)-β-hydroxypalmitic acid

C: 4298-08-2
trans-3-hydroxy-L-proline

D: 51-35-4
4R-4-hydroxyproline

Conditions

Conditions	Yield
With hydrogenchloride at 110℃; for 16h;	A 14.7 mg B 19 mg C 14.2 mg D 15.6 mg

...Expand

: (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carboxylic acid methyl ester

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With Dowex 50W-X8; water In tetrahydrofuran Heating;	0.14 g

: 147-85-3
L-proline

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
With α-ketoglutaric acid; iron(II) sulfate; ascorbic acid; Aeromonas caviae In water at 25℃; for 24h; pH=7; Enzymatic reaction;

: (2R,3S)-1-Benzyl-3-hydroxy-pyrrolidine-2-carbonitrile

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / aq. hydrochloric acid / 8 h / 45 - 50 °C 2: 98 percent / H2 / Pd-C / methanol / 13 h / 20 °C View Scheme

: 404369-20-6
methyl (2S,3S)-3-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 98 percent / imidazole / dimethylformamide / 12 h / 20 °C 2.1: BH3*SMe2 / tetrahydrofuran / 10 h / 20 °C 2.2: 70 percent / NaOH; aq. H2O2 / tetrahydrofuran 3.1: 87 percent / MsCl; Et3N / tetrahydrofuran / 3 h / 0 °C 4.1: H2 / Pd/C / methanol / 3 h / 60 °C 5.1: 0.14 g / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

: (2S,3S)-1-Allyl-3-hydroxy-pyrrolidine-2-carboxylic acid amide

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Amberlyst 15 / 65 °C 2: 70 percent / 1.) Pd(dba)2, Dppb, mercaptobenzoic acid, 2.) 1M HCl / tetrahydrofuran / Ambient temperature 3: 88 percent / KOH / methanol; H2O / Ambient temperature View Scheme

: 213131-33-0
(2S,3S)-1-Allyl-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / 1.) Pd(dba)2, Dppb, mercaptobenzoic acid, 2.) 1M HCl / tetrahydrofuran / Ambient temperature 2: 88 percent / KOH / methanol; H2O / Ambient temperature View Scheme

: 213131-29-4
(2R,3S)-1-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonitrile

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: HCl / methanol / -20 °C 2: Amberlyst 15 / 65 °C 3: 70 percent / 1.) Pd(dba)2, Dppb, mercaptobenzoic acid, 2.) 1M HCl / tetrahydrofuran / Ambient temperature 4: 88 percent / KOH / methanol; H2O / Ambient temperature View Scheme

: 134107-65-6
(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h 2: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h 3: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 4: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 5: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 6: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 7: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h
2: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h
3: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C
4: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h
5: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr
6: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature
7: 70 percent / 6 M aq. HCl / 3 h / Heating
View Scheme

: 103201-79-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) n-BuLi, hexamethyldisilazane / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h 2: 30percent aq. H2O2 / ethyl acetate / 0.67 h / 0 - 22 °C 3: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h 4: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h 5: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 6: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 7: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 8: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 9: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

Yield

Multi-step reaction with 9 steps
1: 1.) n-BuLi, hexamethyldisilazane / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h
2: 30percent aq. H2O2 / ethyl acetate / 0.67 h / 0 - 22 °C
3: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h
4: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h
5: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C
6: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h
7: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr
8: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature
9: 70 percent / 6 M aq. HCl / 3 h / Heating
View Scheme

: 156045-79-3
bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 2: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 3: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 4: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 5: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

: 156045-81-7
(2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 2: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 3: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

: 156129-73-6
tert-butyl (2R,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)pyrrolidine-1-carboxylate

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 2: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

: 156045-80-6
(2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 2: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 3: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 4: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

: (3R,7aS)-3-phenyl-6-(phenylselanyl)tetrahydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 30percent aq. H2O2 / ethyl acetate / 0.67 h / 0 - 22 °C 2: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h 3: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h 4: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 5: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 6: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 7: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 8: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

Yield

Multi-step reaction with 8 steps
1: 30percent aq. H2O2 / ethyl acetate / 0.67 h / 0 - 22 °C
2: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h
3: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h
4: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C
5: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h
6: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr
7: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature
8: 70 percent / 6 M aq. HCl / 3 h / Heating
View Scheme

: 154631-82-0
(2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h 2: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 3: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 4: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 5: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 6: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h
2: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C
3: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h
4: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr
5: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature
6: 70 percent / 6 M aq. HCl / 3 h / Heating
View Scheme

: C51H89N11O18

A: 736129-34-3
L-erythro-3-amino-butane-1,2,4-triol

B: 56-45-1
L-serin

C: 72-19-5
L-threonine

D: 74-79-3
L-arginine

E: 7298-98-8
2-(S)-amino-3-(R)-hydroxysuccinic acid

F: 4298-08-2
trans-3-hydroxy-L-proline

G: 147-85-3
L-proline

H: 221695-92-7
(R)-3-hydroxy-13-methyltetradecanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water for 20h; Reflux;

...Expand

: C51H89N11O18

A: 56-45-1
L-serin

B: 72-19-5
L-threonine

C: 29621-86-1
(2S,3S)-3-amino-2,4-dihydroxy-butyric acid

D: 74-79-3
L-arginine

E: 21768-43-4
2-amino-2-deoxy-L-erythronic acid

F: 4298-08-2
trans-3-hydroxy-L-proline

G: 147-85-3
L-proline

H: 221695-92-7
(R)-3-hydroxy-13-methyltetradecanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water for 20h; Reflux;

...Expand

: tripropeptin C

A: 56-45-1
L-serin

B: 72-19-5
L-threonine

C: 74-79-3
L-arginine

D: 1186-90-9, 1860-87-3, 4294-45-5, 5174-55-0, 5753-30-0, 6532-76-9, 7298-98-8, 7298-99-9, 16417-36-0, 71653-06-0, 81601-40-3
L-threo-3-hydroxyaspartic acid

E: 7298-98-8
2-(S)-amino-3-(R)-hydroxysuccinic acid

F: 4298-08-2
trans-3-hydroxy-L-proline

G: 147-85-3
L-proline

H: 221695-92-7
(R)-3-hydroxy-13-methyltetradecanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water for 20h; Reflux;

...Expand

: 147-85-3
L-proline

A: 4298-08-2
trans-3-hydroxy-L-proline

B: 51-35-4
4R-4-hydroxyproline

Conditions

Conditions	Yield
With His-tagged eukaryotic α-ketoglutarate/FeII-dependent proline hydroxylase F from Glarea lozoyensis ATCC 74030; ascorbate; α-ketoglutarate; iron(II) sulfate In aq. buffer at 20℃; for 1h; pH=6; Kinetics; Enzymatic reaction; stereoselective reaction;

: (S,S)-N-(1)-benzyl-2-(tert-butoxycarbonyl)-3-acetoxypyrrolidine-2-carboxylate

: 4298-08-2
trans-3-hydroxy-L-proline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 25% Pd(OH)2/C; acetic acid / methanol; water / 20 °C / 3800.26 Torr 2: hydrogenchloride / water / 16 h / 20 °C View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: 4298-08-2
trans-3-hydroxy-L-proline

: 187039-57-2
(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃;	100%
With sodium hydroxide In tetrahydrofuran; water	100%
With sodium hydroxide In tetrahydrofuran	92%

: 67-56-1
methanol

: 4298-08-2
trans-3-hydroxy-L-proline

: 496841-04-4
(2S,3S)-methyl 3-hydroxypyrrolidine-2-carboxylate

Conditions

Conditions	Yield
With thionyl chloride	100%
With thionyl chloride
With hydrogenchloride

: 67-56-1
methanol

: 4298-08-2
trans-3-hydroxy-L-proline

: (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃;	100%
With hydrogenchloride at 0 - 20℃;	99%
With thionyl chloride at 0℃; for 16h;	99%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 4298-08-2
trans-3-hydroxy-L-proline

: 296774-32-8
(2S,3S)-(3-hydroxy)pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane at 0 - 20℃; for 9h;	98%
With sodium hydrogencarbonate In 1,4-dioxane at 0 - 20℃; for 9h;	98%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 3h;	59%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 3h;	59.2%
With sodium hydrogencarbonate In 1,4-dioxane; water at 4 - 20℃; for 10h;	58%

: 67-56-1
methanol

: 24424-99-5
di-tert-butyl dicarbonate

: 4298-08-2
trans-3-hydroxy-L-proline

: 184046-78-4
(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
Stage #1: methanol; trans-3-hydroxy-L-proline With thionyl chloride at 0 - 20℃; for 16h; Stage #2: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 20℃; for 2h;	96%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 100-39-0
benzyl bromide

: 4298-08-2
trans-3-hydroxy-L-proline

: 330945-07-8
2-benzyl 1-(tert-butyl) (2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; trans-3-hydroxy-L-proline With sodium hydroxide; water In tetrahydrofuran at 20℃; for 19h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Stage #3: benzyl bromide With hydrogenchloride; potassium hydrogencarbonate more than 3 stages;	91%

...Expand

: 67-56-1
methanol

: 4298-08-2
trans-3-hydroxy-L-proline

: methyl (3S)-3-hydroxy-L-prolinate hydrochloride

Conditions

Conditions	Yield
With acetyl chloride at 0 - 65℃; for 6h;	91%

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 4298-08-2
trans-3-hydroxy-L-proline

: 187039-57-2
(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; methanol; water at 20℃; for 4h;	88%
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 12h;

: 35661-40-6
N-Fmoc L-Phe

: 4298-08-2
trans-3-hydroxy-L-proline

: 847978-88-5
(2S,3S)-1-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-3-hydroxy-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Stage #1: N-Fmoc L-Phe With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; Stage #2: trans-3-hydroxy-L-proline With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;	88%

: 4298-08-2
trans-3-hydroxy-L-proline

: 501-53-1
benzyl chloroformate

: 62182-54-1
(2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water for 20h;	78%
With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 0 - 20℃;
With sodium hydrogencarbonate

: 34619-03-9
tert-butyldicarbonate

: 4298-08-2
trans-3-hydroxy-L-proline

: 187039-57-2
(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water for 24h;	75%

: 4298-08-2
trans-3-hydroxy-L-proline

: 104-15-4
toluene-4-sulfonic acid

: 115-11-7
isobutene

: 3(S)-tert-butoxy-L-proline tert-butyl ester tosylate

Conditions

Conditions	Yield
In dichloromethane at -78 - 20℃; for 72h;	72%

...Expand

: 67-56-1
methanol

: 76-83-5
trityl chloride

: 4298-08-2
trans-3-hydroxy-L-proline

: 401909-57-7
(2S,3S)-1-(triphenylmethyl)-3-hydroxyproline methyl ester

Conditions

Conditions	Yield
Stage #1: methanol; trans-3-hydroxy-L-proline With thionyl chloride Stage #2: trityl chloride With triethylamine In dichloromethane at 0 - 20℃;	72%

...Expand

: 4298-08-2
trans-3-hydroxy-L-proline

: 115-11-7
isobutene

: trans-3-tert-butoxy-L-proline

Conditions

Conditions	Yield
Stage #1: trans-3-hydroxy-L-proline; isobutene With toluene-4-sulfonic acid In dichloromethane at -78 - 20℃; for 72h; Stage #2: With sodium hydroxide In dichloromethane; water at 0℃; for 4h; Stage #3: With hydrogenchloride In dichloromethane; water at 0℃; for 0.5h;	69%

: 4298-08-2
trans-3-hydroxy-L-proline

: 103979-54-0
1H,2H,4H-thieno[2,3-d][1,3]oxazine-2,4-dione

: 1140528-76-2
(8S,8aS)-8-hydroxy-6,7,8,8a-tetrahydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine-4,9(10H)-dione

Conditions

Conditions	Yield
In water Reflux; regioselective reaction;	35%

: 4298-08-2
trans-3-hydroxy-L-proline

: 529-23-7
2-aminobenzaldehyde

: 55727-58-7
1,2,3,3a,4,9-hexahydro-pyrrolo[2,1-b]quinazolin-3-ol

Conditions

Conditions	Yield
In butan-1-ol at 150℃; for 0.25h; Microwave irradiation; Sealed tube; regioselective reaction;	11%

: 705-21-5
3,5-dichlorobenzensulfonyl chloride

: 4298-08-2
trans-3-hydroxy-L-proline

: 425403-87-8
(2S,3S)-1-(3,5-Dichloro-benzenesulfonyl)-3-hydroxy-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃;

: 4298-08-2
trans-3-hydroxy-L-proline

: 496841-07-7
(2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / HCl / 0 - 20 °C 2: 80 percent / Et3N / CH2Cl2 / 0 - 20 °C 3: 90 percent / PPh3; DEAD / tetrahydrofuran / 9 h / 0 - 20 °C View Scheme

: 4298-08-2
trans-3-hydroxy-L-proline

: 850003-05-3
(2S,3S)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-pyrrolidinecarboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / HCl / 0 - 20 °C 2: 80 percent / Et3N / CH2Cl2 / 0 - 20 °C 3: 90 percent / i-Pr2NEt / DMAP / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetyl chloride / 6 h / 0 - 65 °C 2: sodium hydrogencarbonate / tetrahydrofuran; water / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 3.5 h View Scheme
Multi-step reaction with 3 steps 1: acetyl chloride / 20 h / 0 - 65 °C 2: sodium hydrogencarbonate / tetrahydrofuran / 10 h / 0 - 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetyl chloride / 0 - 65 °C / Cooling with ice bath; Inert atmosphere 2: sodium hydrogencarbonate / tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere; Cooling with ice bath 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / 6.17 h / 0 - 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: 1H-imidazole / dichloromethane / 20 °C View Scheme

L-Proline, 3-hydroxy-,(3S)- Specification

The L-Proline, 3-hydroxy-,(3S)-, with CAS registry number 4298-08-2, belongs to the following product category: Pyrrolidine series. It has the systematic name of (3S)-3-hydroxy-D-proline. Besides this, it is also called Trans-3-hydroxy-l-proline. This chemical is a kind of white to light beige powder. When use it, do not breathe dust and avoid contact with skin and eyes. And the chemical formula of this chemical is C₅H₉NO₃.

Physical properties of L-Proline, 3-hydroxy-,(3S)-: (1)ACD/LogP: -0.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4; (4)ACD/LogD (pH 7.4): -4; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 69.56 Å²; (13)Index of Refraction: 1.54; (14)Molar Refractivity: 29.493 cm³; (15)Molar Volume: 93.985 cm³; (16)Polarizability: 11.692×10^-24cm³; (17)Surface Tension: 62.248 dyne/cm; (18)Density: 1.395 g/cm³; (19)Flash Point: 168.639 °C; (20)Enthalpy of Vaporization: 69.507 kJ/mol; (21)Boiling Point: 355.233 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@@H]1NCC[C@@H]1O
(2)InChI: InChI=1/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1
(3)InChIKey: BJBUEDPLEOHJGE-IUYQGCFVBS
(4)Std. InChI: InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1
(5)Std. InChIKey: BJBUEDPLEOHJGE-IUYQGCFVSA-N

Product Name

L-Proline, 3-hydroxy-,(3S)-

Synthetic route

L-Proline, 3-hydroxy-,(3S)- Specification

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