1-[4-(Tert-butyldimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one → 1-(4-Hydroxy-cyclohexyl)-3-(3-methyl-benzofuran-2-ylmethyl)-pyrrolidin-2-one

HRID 1173831Notes

Reaction equation

HRID 1173831 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)(C)(C)C.Br[CH2:22][C:23]1[O:24][C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27]=1[CH3:28]>>[OH:6][CH:7]1[CH2:8][CH2:9][CH:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:22][C:23]3[O:24][C:25]4[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=4[C:27]=3[CH3:28])[C:14]2=[O:18])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 592994751-[4-(Tert-butyldimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-oneHCID 595573982-(Bromomethyl)-3-methyl-1-benzofuran

Product 1

HCID 116598911-(4-Hydroxy-cyclohexyl)-3-(3-methyl-benzofuran-2-ylmethyl)-pyrrolidin-2-oneYield 54%

Procedure

Using the procedure to synthesize Example 3 and using reagents 1-[4-(tert-butyldimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (500 mg, 1.68 mmol) and 2-bromomethyl-3-methyl-benzofuran (567 g, 2.52 mmol) afford the title compound as a tan powder (295 mg, 54%): Mass spectrum (apci) m/z=328.1 (M+H).

Workup

  1. customto synthesize Example 3

Sources & evidence

ORD record
ord-720a6fe720a94c4da0fb9d08db0d5696
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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