5-[3-(Tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-pyrrolidin-2-one → 4-{2-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acid ethyl ester

HRID 2219703Notes

Reaction equation

C([Si](C)(C)OC(CC1C=CC=CC=1)CCC1NC(=O)CC1)(C)(C)C.[CH2:25]([O:27][C:28](=[O:62])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]2[C:42](=[O:43])[CH2:41][CH2:40][CH:39]2[CH2:44][CH2:45][CH:46]([O:54][Si](C(C)(C)C)(C)C)[CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:31][CH:30]=1)[CH3:26]>>[CH2:25]([O:27][C:28](=[O:62])[C:29]1[CH:30]=[CH:31][C:32]([O:35][CH2:36][CH2:37][N:38]2[C:42](=[O:43])[CH2:41][CH2:40][CH:39]2[CH2:44][CH2:45][CH:46]([OH:54])[CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:33][CH:34]=1)[CH3:26]

Participants

Reactant 2

HCID 129700855-[3-(Tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-pyrrolidin-2-one

HCID 692713194-(2-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-5-oxo-pyrrolidin-1-yl}-ethoxy)-benzoic acid ethyl ester

Product 1

HCID 692703774-{2-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acid ethyl esterYield 100.2%

Procedure

Analogous to the procedure described for Compound 1A, Step E, 4-(2-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-5-oxo-pyrrolidin-1-yl}-ethoxy)-benzoic acid ethyl ester (66.4 mg, 0.122 mmol) was deprotected to provide 4-{2-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acid ethyl ester (52 mg) after purification by radial chromatography (CH2Cl2 to 2% MeOH in CH2Cl2). 1H NMR (CDCl3) δ 7.94 (m, 2H), 7.31-7.16 (m, 5H), 6.83 (m, 2H), 4.30 (q, 2H), 4.12 (m, 2H), 3.90 (m, 1H), 3.76 (m, 2H), 3.38 (m, 1H), 2.80 (m, 1H), 2.64 (m, 1H), 2.33 (m, 2H), 2.10 (m, 1H), 1.69-1.37 (m, 6H), 1.34 (t, 3H).

Sources & evidence

ORD record: ord-59559b4f6cf74612b0ffbe0e77b6a779
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414071B2

Reaction notes

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