Sodium bis(trimethylsilyl)amide → 4-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester

HRID 2219682Notes

Reaction equation

HRID 2219682 reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][CH:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[CH2:8][CH2:9][CH:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:39][O:40][C:41](=[O:52])[C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][CH2:50]Br)=[CH:44][CH:43]=1>>[CH3:39][O:40][C:41](=[O:52])[C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][CH2:50][N:14]2[C:13](=[O:15])[CH2:12][CH2:11][CH:10]2[CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:28])[CH3:27])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=2)=[CH:44][CH:43]=1

Participants

4

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10801120Methyl 4-(3-bromopropyl)benzoateHCID 129700985-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one

Product 1

HCID 129700994-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl esterYield 84.2%

Procedure

Analogous to the procedure described for Compound 1A, Step D, 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one (250 mg, 0.602 mmol) was alkylated with NaHMDS (1M in THF, 0.72 mL, 0.72 mmol) and 4-(3-bromo-propyl)-benzoic acid methyl ester (170 mg, 0.663 mmol) to yield 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (300 mg). MS 592.1 (M+1).

Sources & evidence

ORD record
ord-84be8e1073c34ace95189eba5bd814c3
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

Loading…