(+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate
• CAS No.: 1308799-02-1
• Molecular Formula: C₂₁H₃₅NO₄Si
• Molecular Weight: 393.599
• Mol file: 1308799-02-1.mol

Synonyms:(+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate

Chemical Property of (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate

There total 4 articles about (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate 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: 75.0%

1-bromo-4-methoxy-benzene (104-92-7) + (+/-)-tert-butyl {2-methyl-2-[(trimethylsilyl)oxy]pent-4-en-1-yl}carbamate (1308799-00-9) → (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate (1308799-02-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; sodium t-butanolate; In toluene; at 20 - 90 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ol2009895

Reference yield:

tert-butyl 2-hydroxypropylcarbamate (95656-86-3,119768-44-4,138457-45-1) → (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate (1308799-02-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium chlorochromate / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

2: diethyl ether / 0 - 20 °C / Inert atmosphere

3: 4 h / 20 °C / Inert atmosphere

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; sodium t-butanolate / toluene / 14 h / 20 - 90 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; pyridinium chlorochromate; sodium t-butanolate; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/ol2009895

Reference yield:

(+/-)-1-(N-tert-Butoxycarbonylamino)propan-2-one (170384-29-9) → (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate (1308799-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether / 0 - 20 °C / Inert atmosphere

2: 4 h / 20 °C / Inert atmosphere

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; sodium t-butanolate / toluene / 14 h / 20 - 90 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; sodium t-butanolate; In diethyl ether; toluene;

DOI:10.1021/ol2009895

upstream raw materials:

1-bromo-4-methoxy-benzene

(+/-)-tert-butyl {2-methyl-2-[(trimethylsilyl)oxy]pent-4-en-1-yl}carbamate

(+/-)-tert-butyl (2-hydroxy-2-methylpent-4-en-1-yl)carbamate

tert-butyl 2-hydroxypropylcarbamate

Downstream raw materials:

(+)-(5S)-5-(4-methoxybenzyl)-3-methyl-1-tosylpyrrolidin-3-ol

(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

(1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine

(+)-(2S)-tert-butyl 4-hydroxy-2-(4-methoxybenzyl)-4-methylpyrrolidine-1-carboxylate