N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine
• CAS No.: 207227-19-8
• Molecular Formula: C₃₁H₃₉NO₃Si
• Molecular Weight: 501.741
• Mol file: 207227-19-8.mol

Synonyms:N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine

Chemical Property of N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine

There total 5 articles about N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]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: 55.0%

N-(benzyloxycarbonyl)-(2R)-2-[(1S,2S)-1-chloromercurio-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine → N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine (207227-19-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 20 - 60 ℃; for 2h;

DOI:10.1016/S0957-4166(01)00064-7

Reference yield:

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal (87696-33-1) → N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine (207227-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / tetrahydrofuran / 0 °C

2: 91 percent / LiAlH₄ / diethyl ether / 1 h / Heating

3: 87 percent / toluene / 24 h / Ambient temperature

4: 1) Hg(OAc)2, 2) Bu₃SnH, AIBN / 1) CH₂Cl₂, RT, 3 d, 2) toluene

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); mercury(II) diacetate; tri-n-butyl-tin hydride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/S0040-4039(98)00253-6

Reference yield:

(4Z,6S)-6-[(tert-butyldiphenylsilyl)oxy]-4-heptenamine (207227-14-3) → N-(benzyloxycarbonyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine (207227-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / toluene / 24 h / Ambient temperature

2: 1) Hg(OAc)2, 2) Bu₃SnH, AIBN / 1) CH₂Cl₂, RT, 3 d, 2) toluene

With 2,2'-azobis(isobutyronitrile); mercury(II) diacetate; tri-n-butyl-tin hydride; In toluene;

DOI:10.1016/S0040-4039(98)00253-6

upstream raw materials:

N-(benzyloxycarbonyl)-(4Z,6S)-6-[(tert-butyldiphenylsilyl)oxy]-4-heptenamine

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

(4Z,6S)-6-[(tert-butyldiphenylsilyl)oxy]-4-heptenamine

(4Z,6S)-6-[(tert-butyldiphenylsilyl)oxy]-4-heptenenitrile

Downstream raw materials:

N-(methyl)-(2R)-2-[(2S)-2-((tert-butyldiphenylsilyl)oxy)prop-1-yl]pyrrolidine