(2-Bromoethoxy)-tert-butyldimethylsilane → (S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 912437Notes

Reaction equation

HRID 912437 reaction equation
[O:1]=[C:2]1[C@@H:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][CH2:4][NH:3]1.Br[CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[Si:19]([O:18][CH2:17][CH2:16][N:3]1[CH2:4][CH2:5][C@H:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[C:2]1=[O:1])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate

Product 1

HCID 57736552(S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-ylcarbamateYield 37%

Procedure

(S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidin-3-ylcarbamate was prepared from compound (s)-tert-butyl 2-oxopyrrolidin-3-ylcarbamate (Example 6) and (2-bromoethoxy)(tert-butyl)dimethylsilane according to the general procedure of Example 9. The crude product was purified by column chromatography, eluting with 80% ethyl acetate/hexanes, to provide compound (2b) in 37% yield.

Workup

  1. customThe crude product was purified by column chromatography
  2. washeluting with 80% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-90d94143a2464ad7b9537d387ab82ff2
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

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