6216-63-3

Basic information

• Product Name: (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE
• Synonyms: (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE;(S)-N-BENZYLOXYCARBONYL-2-HYDROXYMETHYLPYRROLIDONE;N-BENZYLOXYCARBONYL-L-PROLINOL;N-CBZ-L-PROLINOL;Z-L-PROLINOL;Z-L-PRO-OL;CBZ-L-prolinol;(S)-(-)-1-(BENZYLOXYCARBONYL)-2 -PYRROLIDINEMETHANOL
• CAS NO: 6216-63-3
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.28
• Product Categories: pharmacetical
• Mol File: 6216-63-3.mol
• Article Data: 67

Chemical Properties

• Boiling Point: 160 °C0.8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.196 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.54(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.77±0.10(Predicted)
• CAS DataBase Reference: (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE(6216-63-3)
• EPA Substance Registry System: (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE(6216-63-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6216-63-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to orange liquid

InChI:InChI=1/C13H17NO3/c15-9-12-7-4-8-14(12)13(16)17-10-11-5-2-1-3-6-11/h1-3,5-6,12,15H,4,7-10H2/t12-/m0/s1

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 7664-93-9 sulfuric acid 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 105414-01-5 Cbz-L-Pro-OCO₂-i-Bu 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 75-03-6 ethyl iodide 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 501-53-1 benzyl chloroformate 
• 200499-64-5 (2S,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine 
• 200499-59-8 (S)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 
• 200499-65-6 (S)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine 
• 200499-61-2 (S)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde 
• 200499-62-3 (S)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine 

Downstream Products

• 86954-06-5 1-Z-2-(bromomethyl)pyrrolidine 
• 128359-99-9 (2S)-1-(Benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidine 
• 15791-08-9 4,6-dichloro-2-hydroxy-1,3,5-triazine 
• 175892-99-6 ethyl (E)-3-[(2S)-1-(benzyloxycarbonyl)pyrrolidin-2-yl]prop-2-enoate 
• 321745-51-1 tert-butyl (2S)-2-[hydroxy(1-isopropyl-1H-indol-6-yl)methyl]pyrrolidine-1-carboxylate 
• 321745-53-3 tert-butyl (2S)-2-[hydroxy(triisopropylsilyl-1H-indol-6-yl)methyl]pyrrolidine-1-carboxylate 
• 73365-02-3 tert-butoxycarbonyl-D-prolinal 
• 1230072-98-6 benzyl (2S)-2-[2-oxopropyl]pyrrolidine-1-carboxylate 
• 1230073-02-5 1-[(2S)-pyrrolidin-2-yl]acetone 
• 1350627-29-0 benzyl (2S)-2-[(1'E)-2'-nitroprop-1'-en-1'-yl]pyrrolidine-1-carboxylate 
• 929020-33-7 C₁₅H₂₁NO₃ 
• 929020-32-6 C₁₅H₂₁NO₃ 
• 143771-06-6 (-)-(S)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 1446128-16-0 benzyl (2S)-2-[(E)-2-nitrovinyl]pyrrolidine-1-carboxylate 

Relevant articles and documents

Synthesis of pyrrolizidines via Copper(I) catalyzed radical atom transfer cyclization

Trachelanthamidine and pseudoheliotridane are synthesized from (2S)-N-trichloroacetyl-2-vinylpyrrolidine (5) by a 5-exo-trig radical cyclization. The intermediate radical is generated heating 5 in a sealed tube (CH3CN/160°C) using CuCl as catal

Synthesis and absolute configuration of 2-(12'-aminotridecyl)-pyrrolidine, a defensive alkaloid from the Mexican bean beetle, Epilachna varivestis

The synthesis of 2-(12'-aminotridecyl)-pyrrolidine (1), a defensive alkaloid recently isolated from the Mexican bean beetle, Epilachna varivestis, is described. The (2S,12'R) configuration is assigned to this alkaloid by comparing the 1H NMR spectrum of its (S)-MTPA derivative with that of (R)- and (S)-MTPA [α-methoxy-α-(trifluoromethyl)phenylacetyl] derivatives of the synthetic sample. These results suggest that the seventeen carbon skeleton of 1 is acetate rather than proline derived.

Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form

Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.

Syntheses of chiral ferrocenophanes and their application to asymmetric catalysis

N-Substituted 2-aza-[3]-ferrocenophanes were easily synthesized from 1,1′-ferrocenedicarbaldehyde and aliphatic amines in high yields. One of the ferrocenophanes served as a ligand for the copper-catalyzed oxidative coupling of 2-naphthol derivatives to give the products in good yields with up to 92% ee, and it also efficiently catalyzed the asymmetric Michael addition reaction as an organocatalyst.