tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate

Base Information

• Chemical Name: tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate
• CAS No.: 127199-54-6
• Molecular Formula: C10H20N2O2
• Molecular Weight: 200.281
• Mol file: 127199-54-6.mol

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

Chemical Property of tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate

Chemical Property:

• Boiling Point: 295.1±29.0 °C(Predicted)
• PKA: 12.39±0.40(Predicted)
• Density: 1.02±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl(3S,4S)-4-methylpyrrolidin-3-ylcarbamate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate

There total 7 articles about tert-butyl (3S,4S)-4-Methylpyrrolidin-3-ylcarbaMate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(3S,4S)-1-benzyl-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine (127199-52-4) → (3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (127199-54-6,1334481-84-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 40 ℃; for 3h; under 3800 Torr;

DOI:10.1248/cpb.44.1128

Reference yield: 72.1%

(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(phenylsulfanil)methylpyrrolidine (869956-21-8) → (3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (127199-54-6,1334481-84-3)

Guidance literature:

(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(phenylsulfanil)methylpyrrolidine; With hydrogen; In ethanol; at 50 ℃; for 18h;

With hydrogen; palladium 10% on activated carbon; In ethanol; at 20 ℃; for 3h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (127199-54-6,1334481-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1: propan-2-ol / 0.5 h / Ambient temperature

2: NEt₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 71 percent / 72 h / Ambient temperature; var. temp., var,reaction time, var. amounts of reagents

4: 92 percent / H₂ / 5percent Pd/C / methanol / 3 h / 40 °C / 3800 Torr

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; isopropyl alcohol;

DOI:10.1248/cpb.44.1128

upstream raw materials:

(3S,4S)-1-benzyl-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine

di-tert-butyl dicarbonate

(2S,3R)-2-amino-3-methylbutane-1,4-diol

(2S,3R)-2-(tert-butoxycarbonyl)amino-3-methylbutane-1,4-diol

Downstream raw materials:

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

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