Tetrabutylammonium Fluoride → 4-{3-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzonitrile

HRID 2219706Notes

Reaction equation

HRID 2219706 reaction equation
C([Si](C)(C)OC(CC1C=CC=CC=1)CCC1NC(=O)CC1)(C)(C)C.C([Si](C)(C)[O:30][CH:31]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:32][CH2:33][CH:34]1[CH2:38][CH2:37][C:36](=[O:39])[N:35]1[CH2:40][CH2:41][CH2:42][C:43]1[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[CH:45][CH:44]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[OH:30][CH:31]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:32][CH2:33][CH:34]1[CH2:38][CH2:37][C:36](=[O:39])[N:35]1[CH2:40][CH2:41][CH2:42][C:43]1[CH:44]=[CH:45][C:46]([C:47]#[N:48])=[CH:49][CH:50]=1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 129700855-[3-(Tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-pyrrolidin-2-oneHCID 227124384-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzonitrile

Product 1

HCID 227125194-{3-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzonitrileYield 79.8%

Procedure

Analogous to the procedure described for Compound 1A, Step E, 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzonitrile (257.6 mg, 0.525 mmol) was deprotected with TBAF (1M in THF, 0.79 mL, 0.79 mmol) over 24 h. Purification by medium pressure chromatography (1:1 EtOAc: hexanes to EtOAc to 1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2) provided 4-{3-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzonitrile (157.8 mg). 1H NMR (CDCl3) δ 7.56 (m, 2H), 7.26 (m, 7H), 3.80 (m, 1H), 3.67-3.55 (m, 2H), 2.98 (m, 1H), 2.80 (m, 1H), 2.65 (t, 2H), 2.43-2.24 (m, 2H), 2.08 (m, 1H), 1.89-1.33 (m, 9H); MS 375.3 (M−1).

Workup

  1. customPurification by medium pressure chromatography (1:1 EtOAc: hexanes to EtOAc to 1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-cbe764bc88584839b3054baef101ce56
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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