127199-54-6

Basic information

• Product Name: tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate
• Synonyms: tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate;(3S,4S)-3-(Boc-aMino)-4-Methylpyrrolidine;(3S,4S)-(4-Methyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester;[(3S,4S)-4-Methyl-3-pyrrolidinyl]carbamic acid 1,1-dimethylethyl ester
• CAS NO: 127199-54-6
• Molecular Formula: C₁₀H₂₀N₂O₂
• Molecular Weight: 200.278
• EINECS: -0
• Mol File: 127199-54-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 295.1±29.0 °C(Predicted)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 12.39±0.40(Predicted)
• CAS DataBase Reference: tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate(127199-54-6)
• EPA Substance Registry System: tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate(127199-54-6)

Safety Data

• Hazardous Substances Data: 127199-54-6(Hazardous Substances Data)

Usage

General Description

Tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate is a chemical compound with the molecular formula C11H23NO2. It is a derivative of the amino acid proline and belongs to the class of carbamates. tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate is commonly used in the pharmaceutical industry as a chiral building block in the synthesis of various drugs and active pharmaceutical ingredients. It exhibits unique stereochemistry, with specific configurations at the 3rd and 4th positions of the pyrrolidinyl group, and the tert-butyl group adding steric hindrance to the molecule. Tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate is an important intermediate in the production of pharmaceuticals and is utilized for its chirality in asymmetric synthesis.

Upstream product

• 869956-21-8 (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(phenylsulfanil)methylpyrrolidine 
• 178755-12-9 (2S,3R-)-2-[N-Benzyl-N-(9-phenylfluoren-9-yl)]amino-3-methylbutane-1,4-diol 
• 149598-23-2 (2S,3R)-2-(tert-butoxycarbonyl)amino-1,4-bis(methanesulfonyloxy)-3-methylbutane 
• 149598-21-0 (2S,3R)-2-(tert-butoxycarbonyl)amino-3-methylbutane-1,4-diol 
• 178899-79-1 (2S,3R)-2-amino-3-methylbutane-1,4-diol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 127199-52-4 (3S,4S)-1-benzyl-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine 

Downstream Products

• 869956-22-9 ethyl 4-[(3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidin-1-yl]-2,5-difluoro-3-methylbenzoate 

Relevant articles and documents

SUBSTITUTED PYRROLIDINE DERIVATIVE

The present invention contemplates provision of a quinolone antibacterial agent and a drug for the treatment of infectious diseases, which exhibit potent antibacterial activity and higher selective toxicity against Gram-positive and Gram-negative bacteria

A large-scale preparation of (3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine and its analogs from L-aspartic acid

(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (12a) was synthesized from L-aspartic acid (4) on a large scale. Methylation of dimethyl (2S)-N-benzyl-N-(9-phenylfluoren-9-yl)aspartate (5), easily derived from 4, with methyl iodide gave (3R)-3-methylaspartate (6a) in 91% yield with high diastereoselectivity. Reduction of 6a with lithium aluminum hydride, followed by hydrogenolysis, protection with di-tert-butyl dicarbonate, and mesylation gave 10a in 89% overall yield. Subsequently, reaction of 10a with benzylamine under a nitrogen atmosphere at room temperature, followed by hydrogenolysis, gave the target compound (12a) in 65% overall yield. In a similar manner to that described for the preparation of 12a from 5, compound 5 was converted into 4-ethyl and 4-propyl derivatives (12b,c) in 34% and 38% overall yields.