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

Base Information

• Chemical Name: (3R,4S,1'S)-3-(t-butoxycarbonylamino)-4-(hydroxymethyl)-1-(1-phenylethyl)pyrrolidine
• CAS No.: 1050504-30-7
• Molecular Formula: C₁₈H₂₈N₂O₃
• Molecular Weight: 320.432
• Mol file: 1050504-30-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (3R,4S,1'S)-3-(t-butoxycarbonylamino)-4-(hydroxymethyl)-1-(1-phenylethyl)pyrrolidine 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,4R)-4-amino-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]methanol (1050504-29-4) + di-tert-butyl dicarbonate (24424-99-5) → (3R,4S,1'S)-3-(t-butoxycarbonylamino)-4-(hydroxymethyl)-1-(1-phenylethyl)pyrrolidine (1050504-30-7)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 2h;

DOI:10.1007/s00706-014-1251-4

Reference yield:

C20H28N2O6 → (3R,4S,1'S)-3-(t-butoxycarbonylamino)-4-(hydroxymethyl)-1-(1-phenylethyl)pyrrolidine (1050504-30-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1007/s00706-014-1251-4

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;

upstream raw materials:

[(3S,4R)-4-amino-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]methanol

di-tert-butyl dicarbonate

Downstream raw materials:

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

[(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