(3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

Base Information

Chemical Name:(3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine
CAS No.:259264-80-7
Molecular Formula:C₂₇H₃₉NO₄Si
Molecular Weight:469.696
Hs Code.:

Synonyms:(3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

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Chemical Property of (3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

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Technology Process of (3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

There total 4 articles about (3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine 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: 98.0%

: 259264-79-4
(S)-(-)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]pyrrolidin-2-one

: 259264-80-7
(3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;
DOI:10.1021/ja993295t

Reference yield:

: 4294-57-9
para-methylphenylmagnesium bromide

: 259264-80-7
(3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuCN / diethyl ether; tetrahydrofuran / 144 h / 20 °C

1.2: 23 percent / H₂O

2.1: oxalyl chloride; 2,6-lutidine / CH₂Cl₂ / 18 h / 20 °C

2.2: 39 percent / imidazole / dimethylformamide / 7 h / 80 °C

3.1: 95 percent / Et₃N / DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: 98 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; triethylamine; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Alkylation / 1.2: Hydrolysis / 2.1: Acylation / 2.2: Substitution / 3.1: Acylation / 4.1: Reduction;
DOI:10.1021/ja993295t

Reference yield:

: tert-butylbis(4-methylphenyl)silanol

: 259264-80-7
(3S)-1-(tert-butoxycarbonyl)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]-2-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride; 2,6-lutidine / CH₂Cl₂ / 18 h / 20 °C

1.2: 39 percent / imidazole / dimethylformamide / 7 h / 80 °C

2.1: 95 percent / Et₃N / DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: 98 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; triethylamine; dmap; In methanol; dichloromethane; 1.1: Acylation / 1.2: Substitution / 2.1: Acylation / 3.1: Reduction;
DOI:10.1021/ja993295t