N-Methyl-L-prolinol supplier | CasNO.34381-71-0

Name
N-Methyl-L-prolinol
EINECS 251-981-9
CAS No. 34381-71-0
Article Data31
CAS DataBase
Density 0.973 g/cm³
Solubility
Melting Point
Formula C₆H₁₃NO
Boiling Point 164.8 °C at 760 mmHg
Molecular Weight 115.175
Flash Point 63.3 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 23-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Pyrrolidinemethanol,1-methyl-, (S)-;(-)-(S)-1-Methyl-2-pyrrolidinemethanol;(2S)-(Hydroxymethyl)-1-methylpyrrolidine;(2S)-1-Methylpyrrolidin-2-ylmethanol;(2S)-1-Methylpyrrolidine-2-methanol;(S)-(-)-(1-Methyl-2-pyrrolidinyl)methanol;(S)-(-)-1-Methylpyrrolidine-2-methanol;(S)-(-)-2-Hydroxymethyl-1-methylpyrrolidine;(S)-1-Methyl-2-pyrrolidinemethanol;(S)-1-Methylpyrrolidin-2-ylmethanol;(S)-2-(Hydroxymethyl)-1-methylpyrrolidine;(S)-N-Methylpyrrolidine-2-methanol;L-(-)-N-Methyl-2-pyrrolidinylmethanol;L-N-Methylprolinol;2-Pyrrolidinemethanol,1-methyl-, (2S)-;
PSA 23.47000
LogP 0.01080

Synthetic route

: 59936-29-7
(S)-N-(tert-butoxycarbonyl)proline methyl ester

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	90%

: 50-00-0
formaldehyd

: 23356-96-9
(S)-1-Pyrrolidin-2-yl-methanol

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With formic acid In water for 20h; Heating;	65%
With formic acid; water anschliessenden Erhitzen;
With hydrogen; platinum(IV) oxide In water for 24h;	2.4 g
With formic acid
With formic acid Yield given;

: 475-11-6, 58123-62-9, 68078-09-1
N-methyl-L-proline

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;	65%

: 147-85-3
L-proline

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With aq. sodium hydroxide; acetic anhydride In tetrahydrofuran; formic acid; water	57%
Multi-step reaction with 2 steps 1: NaBH4, H2SO4 2: HCOOH View Scheme
Multi-step reaction with 2 steps 1: NaBH4, conc. H2SO4 2: HCOOH View Scheme
Multi-step reaction with 2 steps 1: acetic anhydride / 2 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 48 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 94 percent / H2O 2: 95 percent / diethyl ether 3: 90 percent / 3 eq. LiAlH4 / diethyl ether View Scheme

: 27957-91-1
N-Methyl-L-proline Methyl Ester

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
	53%
With lithium aluminium tetrahydride In tetrahydrofuran

: 1148-11-4
N-Benzyloxycarbonyl-L-proline

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran 1.) room temp., 1 h, 2.) reflux, 3 h;	49%

: 64-18-6
formic acid

: 147-85-3
L-proline

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
Stage #1: formic acid; L-proline With acetic anhydride Stage #2: With lithium aluminium tetrahydride	48%

: 13200-83-4
(2S)-1-formylpyrrolidine-2-carboxylic acid

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating; Yield given;

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride

: 68078-09-1
N-methylproline

A: 3554-65-2, 30727-24-3, 34381-71-0, 99494-01-6
(R)-N-methylpyrrolidine-2-methanol

B: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating; Title compound not separated from byproducts;

<(S)-1-formyl-pyrrolidin-2-yl>-methanol: <(S)-1-formyl-pyrrolidin-2-yl>-methanol

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride; diethyl ether

: 55456-46-7
(S)-(-)-1-Formyl-2-(hydroxymethyl)pyrrolidine

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran

: 2577-48-2
methyl (2S)-pyrrolidine carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium cyanoborohydride 2: LiAlH4 / tetrahydrofuran View Scheme

: 23356-96-9
(S)-1-Pyrrolidin-2-yl-methanol

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: LiAlH4 / tetrahydrofuran View Scheme

: N-Methyl-2-(tributylstannyl)pyrrolidine

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TMEDA, BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg C, 1 h 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

: 15761-39-4
1-(tert-butoxycarbonyl)-L-proline

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / diethyl ether 2: 90 percent / 3 eq. LiAlH4 / diethyl ether View Scheme

: 27871-48-3
(2S)-2-(methoxycarbonyl)-1-methylpyrrolidin-1-ium chloride

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere;	1.2 g

: 4088-84-0
2-fluoro-5-trifluoromethyl-benzonitrile

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 1215230-56-0
(S)-2-((1-methylpyrrolidin-2-yl)methoxy)-5-(trifluoromethyl)benzonitrile

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 3h;	100%
With sodium hydride In tetrahydrofuran at 20℃; for 3h;	100%
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In tetrahydrofuran at 22℃; for 0.333333h; Stage #2: 2-fluoro-5-trifluoromethyl-benzonitrile In tetrahydrofuran at 22℃; for 3h;

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 214360-76-6
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

: 1449321-17-8
(S)-1-methyl-2-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]pyrrolidine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 36h;	100%

: tert-butyl 7-(7-bromo-2-chloro-6-(trifluoromethoxy)quinazolin-4-yl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (S)-7-(7-bromo-2-((1-methylpyrrolidin-2-yl)methoxy)-6-(trifluoromethoxy)quinazolin-4-yl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 1h;	100%

: tert-butyl 4-(2-chloro-6-(naphthalen-1-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (S)-4-(2-((1-methylpyrrolidin-2-yl)methoxy)-6-(naphthalen-1-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: tert-butyl 4-(2-chloro-6-(naphthalen-1-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate In tetrahydrofuran at 60℃; for 3h;	99%

: benzyl (S)-4-(2-chloro-6-(2,3-dimethylbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-2-(cyanomethyl)piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: benzyl (S)-2-(cyanomethyl)-4-(6-(2,3-dimethylbenzyl)-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos In toluene at 105℃; for 16h;	99%

: 88-75-5
2-hydroxynitrobenzene

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 2-[(1-methyl-2(S)-pyrrolidinyl)methoxy]nitrobenzene

Conditions

Conditions	Yield
Stage #1: 2-hydroxynitrobenzene With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 0.166667h; Stage #2: (S)-2-hydroxymethyl-1-methylpyrrolidine for 24h; Mitsunobu reaction;	98%

: 23138-55-8
3-Bromophenyl isocyanate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: (3-bromophenyl)carbamic acid (S)-1-methylpyrrolidin-2-ylmethyl ester

Conditions

Conditions	Yield
In toluene at 50 - 120℃; for 4h;	97%

: 14508-49-7
2-chloropyrazin

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 2-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyrazine

Conditions

Conditions	Yield
With NaH In tetrahydrofuran; mineral oil	97%
With hydrogenchloride; potassium tert-butylate In tetrahydrofuran; water
With hydrogenchloride; potassium tert-butylate In tetrahydrofuran; water
With hydrogenchloride; potassium tert-butylate In tetrahydrofuran; water

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 501-52-0
3-Phenylpropionic acid

: 3-Phenyl-propionic acid (S)-1-methyl-pyrrolidin-2-ylmethyl ester

Conditions

Conditions	Yield
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;	95%

: tert-butyl 4-[6-chloro-8-{[5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]oxy}-2-(methylsulfonyl)pyrido[3,4-d]pyrimidin-4-yl]piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl 4-(6-chloro-8-{[5-chloro-6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]oxy}-2-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}pyrido[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; for 1h;	95%

: 4-(4-bromo-7-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-f]quinazolin-9-yl)piperazine-1-carboxylic acid tert-butyl ester

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: C29H40BrN7O4

Conditions

Conditions	Yield
With caesium carbonate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 170℃; for 3h; Inert atmosphere; Sealed tube;	95%

: 108-88-3
toluene

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: C7H7Li*6C6H12NO(1-)*6Li(1+)

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With n-butyllithium In pentane at -90 - 20℃; Stage #2: toluene In pentane at -30℃; for 24h;	94%

: 4-methyl 1-(4-nitrophenyl) 4-{[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}piperidine-1,4-dicarboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 869189-88-8
4-methyl 1-{[(2S)-1-methylpyrrolidin-2-yl]methyl} 4-{[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}piperidine-1,4-dicarboxylate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3h;	94%

: tert-butyl 4-(7-(6-(bis(4-methoxybenzyl)amino)-3-(trifluoromethyl)pyridin-2-yl)-6-chloro-2-fluoroquinazolin-4-yl)piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (S)-4-(7-(6-(bis(4-methoxybenzyl)amino)-3-(trifluoromethyl)pyridin-2-yl)-6-chloro-2-((1-methylpy rrolidin-2-yl)methoxy)quinazolin-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 0.0833333h; Stage #2: tert-butyl 4-(7-(6-(bis(4-methoxybenzyl)amino)-3-(trifluoromethyl)pyridin-2-yl)-6-chloro-2-fluoroquinazolin-4-yl)piperazine-1-carboxylate In tetrahydrofuran; mineral oil at 25℃; for 1h;	93.4%

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 67824-38-8
(S)-(-)-1-methyl-2-chloromethylpyrrolidine hydrochloride

Conditions

Conditions	Yield
With thionyl chloride In ethanol 1.) RT, 2 h, 2.) reflux, 30 min;	93%
With thionyl chloride In chloroform 1.) room temp., 30 min, 2.) reflux, 30 min;	88%
With hydrogenchloride; thionyl chloride In chloroform for 2h; Heating;	85%

: 16842-00-5, 855944-65-9
trimethylamine alane

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: [(-)-(S)-1-methylpyrrolidino-2-methoxy]alane dimer

Conditions

Conditions	Yield
In toluene byproducts: H2, N(CH3)3; under Ar using Schlenk techniques; soln. N-methyl-L-prolinol added dropwise to soln. AlH3*NMe3 (1:1 mol) in toluene with stirring until gas evolution was ceased; stirring 1 h; repeated crystns. at -78°C; elem. anal.;	90.4%

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 221087-79-2
2-(2,5-dimethylpyrrolyl)-6-(4-fluoronaphth-1-yl)pyridine

: 675846-20-5
2-(2,5-dimethylpyrrolyl)-6-(4-(1-methylpyrrolidin-2-ylmethoxy)naphth-1-yl)pyridine

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In N,N-dimethyl-formamide at 70℃; Stage #2: 2-(2,5-dimethylpyrrolyl)-6-(4-fluoronaphth-1-yl)pyridine In N,N-dimethyl-formamide at 80℃; for 2h;	90%

: 112-82-3
hexadecanyl bromide

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 145707-12-6
Br(1-)*C22H46NO(1+)

Conditions

Conditions	Yield
In acetone for 72h; Reflux;	90%
In acetone at 50℃; for 48h;	73%
In 1,4-dioxane for 48h; Reflux;

: 4-(7-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylic acid tert-butyl ester

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (S)-4-(7-benzyl-2-((1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 6h; Inert atmosphere;	90%
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 4-(7-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; mineral oil at 70℃; for 11h;
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 4-(7-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; mineral oil at 0 - 70℃; for 11h;

: 100-02-7
4-nitro-phenol

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 4-[(1-methyl-2(S)-pyrrolidinyl)methoxy]nitrobenzene

Conditions

Conditions	Yield
Stage #1: 4-nitro-phenol With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 0.166667h; Stage #2: (S)-2-hydroxymethyl-1-methylpyrrolidine for 24h; Mitsunobu reaction;	89%

: 137156-22-0, 171878-71-0, 155613-52-8
binaphthol chlorophosphite

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 479253-14-0
(2'S)-2-[(1'-methyl-pyrrolidinyl-2')-methoxy]dinaphtho[2,1-d:1',2'-f](1,3,2)dioxaphosphepine

Conditions

Conditions	Yield
With triethylamine In toluene	89%

: tert-butyl (2S)-2-(cyanomethyl)-4-((6R)-2-(methylsulfinyl)-3‘,4’,5,7-tetrahydro-1‘Hspiro[cyclopenta[d]pyrimidine-6,2’-naphthalen]-4-yl)piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (S)-2-(cyanomethyl)-4-((R)-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)-3',4’,5,7-tetrahydro-1‘H-spiro[cyclopenta[d]pyrimidine-6,2’-naphthalen]-4-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With potassium tert-butylate In tetrahydrofuran for 0.0833333h; Stage #2: tert-butyl (2S)-2-(cyanomethyl)-4-((6R)-2-(methylsulfinyl)-3‘,4’,5,7-tetrahydro-1‘Hspiro[cyclopenta[d]pyrimidine-6,2’-naphthalen]-4-yl)piperazine-1-carboxylate In tetrahydrofuran at 0℃; for 0.5h;	88%

: 4-((S)-4-((benzyloxy)carbonyl)-3-(cyanomethyl)piperazin-1-yl)-2-(methylsulfoxide)-5,6,7,9-tetrahydro-8H-pyrimidine[4,5-c]azepane-8-carboxylic acid tert-butyl ester

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 4-((S)-4-(benzyloxycarbonyl)-3-(cyanomethyl)piperazin-1-yl)-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)-6,7-dihydro-5H-pyrimido[4,5-c]azepane-8(9H)-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium t-butanolate In toluene for 0.5h; Cooling with ice;	88%

: tert-butyl (S)-4-(7-bromo-2,6-dichloroquinazolin-4-yl)-3-methylpiperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (S)-4-(7-bromo-6-chloro-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)quinazolin-4-yl)-3-methylpiperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxymethyl-1-methylpyrrolidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: tert-butyl (S)-4-(7-bromo-2,6-dichloroquinazolin-4-yl)-3-methylpiperazine-1-carboxylate In N,N-dimethyl-formamide at 0℃; for 1h;	85.6%

: 636-93-1
5-nitroguaiacol

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: (S)-1-Methyl-2-(2-methoxy-5-nitrophenoxy)-pyrrolidine

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran	85%

: benzyl (2S)-2-(cyanomethyl)-4-(2-methylsulfinyl-5,6-dihydrobenzo[h]quinazolin-4-yl)piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: benzyl (2S)-2-(cyanomethyl)-4-[2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]-5,6-dihydrobenzo[h]quinazolin-4-yl]piperazine-1-carboxylate

Conditions

Conditions	Yield
With sodium t-butanolate In toluene for 1h; Cooling with ice;	85%

: 7-benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: (S)-7-benzyl-4-methoxy-2-((1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; ruphos In toluene at 110℃; for 8h; Inert atmosphere;	83%

: tert-butyl (2S)-4-(2’-chloro-3,4,5’,8’-tetrahydro-2H,6’H-spiro[naphthalene-1,7’-quinazolin]-4’-yl)-2-(cyanomethyl)piperazine-1-carboxylate

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: tert-butyl (2S)-2-(cyanomethyl)-4-(2’-(((S)-1-methylpyrrolidin-2-yl)methoxy)-3,4,5’,8’-tetrahydro-2H,6’H-spiro[naphthalene-1,7’-quinazolin]-4’-yl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); [2'-(diphenylphosphanyl)-[1,1'-binaphthalen]-2-yl]diphenylphosphane; sodium t-butanolate In toluene at 110℃; for 2h; Inert atmosphere;	83%

: 34381-71-0
(S)-2-hydroxymethyl-1-methylpyrrolidine

: 137892-92-3
(S)-2-(chloromethyl)-1-methylpyrrolidine

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane	82%
With thionyl chloride
With tetrachloromethane; triphenylphosphine In acetonitrile Heating;

N-Methyl-L-prolinol Chemical Properties

Molecule structure of N-Methyl-L-prolinol (CAS NO.34381-71-0):

IUPAC Name: (1-Methylpyrrolidin-2-yl)methanol
Molecular Weight: 115.17352 g/mol
Molecular Formula: C₆H₁₃NO
Density: 0.973 g/cm³
Boiling Point: 164.8 °C at 760 mmHg
Flash Point: 63.3 °C
Index of Refraction: 1.468
Molar Refractivity: 32.95 cm³
Molar Volume: 118.3 cm³
Surface Tension: 32.2 dyne/cm
Enthalpy of Vaporization: 46.74 kJ/mol
Vapour Pressure: 0.649 mmHg at 25 °C
Storage Temp.: −20 °C
XLogP3-AA: 0.1
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 115.099714
MonoIsotopic Mass: 115.099714
Topological Polar Surface Area: 23.5
Heavy Atom Count: 8
Canonical SMILES: CN1CCCC1CO
InChI: InChI=1S/C6H13NO/c1-7-4-2-3-6(7)5-8/h6,8H,2-5H2,1H3
InChIKey: VCOJPHPOVDIRJK-UHFFFAOYSA-N
EINECS: 251-981-9
Product Categories: chiral;Chiral Reagent

N-Methyl-L-prolinol Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-36-26
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
F: 8-10-23
Hazard Note: Irritant

N-Methyl-L-prolinol Specification

N-Methyl-L-prolinol (CAS NO.34381-71-0) is also named as (1-Methyl-2-pyrrolidinyl)methanol ; (1-Methylpyrrolidin-2-yl)methanol ; 2-Pyrrolidinemethanol, 1-methyl- ; 1-Methyl-2-pyrrolidinemethanol ; 1-Methylpyrrolidine-2-Methanol . N-Methyl-L-prolinol (CAS NO.34381-71-0) is white to light yellow crystal powder.

Product Name

N-Methyl-L-prolinol

Synthetic route

N-Methyl-L-prolinol Chemical Properties

N-Methyl-L-prolinol Safety Profile

N-Methyl-L-prolinol Specification

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