t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate

Base Information

• Chemical Name: t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate
• CAS No.: 1050504-31-8
• Molecular Formula: C₂₅H₃₂N₂O₄
• Molecular Weight: 424.54
• Mol file: 1050504-31-8.mol

Synonyms:t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate

Chemical Property of t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate

There total 2 articles about t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate 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: 93.0%

(3R,4S,1'S)-3-(t-butoxycarbonylamino)-4-(hydroxymethyl)-1-(1-phenylethyl)pyrrolidine (1050504-30-7) + benzoyl chloride (98-88-4) → t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate (1050504-31-8)

Guidance literature:

With dmap; 4 A molecular sieve; triethylamine; In dichloromethane; at 0 ℃; for 3h;

Reference yield:

C20H28N2O6 → t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate (1050504-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

2: triethylamine / methanol / 2 h / 20 °C

3: dmap / dichloromethane / 1 h / 20 °C

With dmap; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1007/s00706-014-1251-4

Reference yield: 70.0%

t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]carbamate (1050504-31-8) → [(3S,4R)-4-(t-butoxycarbonylamino)pyrrolidin-3-yl]methyl benzoate (1050504-32-9)

Guidance literature:

With ammonium formate; palladium 10% on activated carbon; In ethanol; at 78 ℃; for 2h;

upstream raw materials:

(3R,4S,1'S)-3-(t-butoxycarbonylamino)-4-(hydroxymethyl)-1-(1-phenylethyl)pyrrolidine

benzoyl chloride

Downstream raw materials:

[(3S,4R)-4-(t-butoxycarbonylamino)pyrrolidin-3-yl]methyl benzoate

[(3S,4R)-4-(t-butoxycarbonylamino)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-yl]methyl benzoate

[(3S,4R)-1-[2-[4-(benzyloxycarbonylamino)-2-oxopyrimidin-1(2H)-yl]acetyl]-4-(t-butoxycarbonylamino)-pyrrolidin-3-yl]methyl benzoate

[(3S,4R)-1-[2-[6-(benzyloxycarbonylamino)-9H-purin-9-yl]acetyl]-4-(t-butoxycarbonylamino)pyrrolidin-3-yl]-methyl benzoate