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

Base Information

Chemical Name:(+)-(2S)-tert-butyl 4-hydroxy-2-(4-methoxybenzyl)-4-methylpyrrolidine-1-carboxylate
CAS No.:1308799-10-1
Molecular Formula:C₁₈H₂₇NO₄
Molecular Weight:321.417
Hs Code.:

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

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

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

There total 5 articles about (+)-(2S)-tert-butyl 4-hydroxy-2-(4-methoxybenzyl)-4-methylpyrrolidine-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: 90.0%

: 1308799-02-1
(+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate

: 1308799-10-1
(+)-(2S)-tert-butyl 4-hydroxy-2-(4-methoxybenzyl)-4-methylpyrrolidine-1-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Inert atmosphere;
DOI:10.1021/ol2009895

Reference yield:

: 1308799-00-9
(+/-)-tert-butyl {2-methyl-2-[(trimethylsilyl)oxy]pent-4-en-1-yl}carbamate

: 1308799-10-1
(+)-(2S)-tert-butyl 4-hydroxy-2-(4-methoxybenzyl)-4-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 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

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 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; tetrabutyl ammonium fluoride; sodium t-butanolate; In tetrahydrofuran; toluene;
DOI:10.1021/ol2009895

Reference yield:

: 95656-86-3,119768-44-4,138457-45-1
tert-butyl 2-hydroxypropylcarbamate

: 1308799-10-1
(+)-(2S)-tert-butyl 4-hydroxy-2-(4-methoxybenzyl)-4-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 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

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 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; tetrabutyl ammonium fluoride; pyridinium chlorochromate; sodium t-butanolate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol2009895