Tetrabutylammonium Fluoride → 7-{2-[4-(3-Fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

HRID 1582665Notes

Reaction equation

HRID 1582665 reaction equation
C([Si](C)(C)[O:6][CH:7]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[F:31][C:27]1[CH:26]=[C:25]([CH2:24][CH:7]([OH:6])[CH2:8][CH2:9][CH:10]2[CH2:14][CH2:13][C:12](=[O:15])[N:11]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])[CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 227187587-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-fluoro-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

Product 1

HCID 227187697-{2-[4-(3-Fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrileYield 71%

Procedure

Following the procedure described for Example 5, Step B, 7-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-fluoro-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (261.7 mg, 0.551 mmol) was deprotected with TBAF (1M in THF, 0.83 mL, 0.83 mmol). The addition was performed at 0° C. and the reaction mixture was stirred at room temperature for 24 h. Purification by medium pressure chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2) provided 7-{2-[4-(3-fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (141 mg). 1H NMR (CDCl3) δ7.32 (m, 1H), 6.98 (m, 3H), 3.86 (m, 1H), 3.64 (m, 2H), 2.99-2.80 (m, 2H), 2.71 (m, 1H), 2.38 (m, 4H), 2.16 (m, 1H), 1.74-1.29 (m, 14H); MS 361.3 (M+1).

Workup

  1. additionThe addition
  2. customwas performed at 0° C.
  3. customPurification by medium pressure chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a2fb2d52988945ffaaf3ce2d156f5ea4
Source dataset
uspto-grants-2004_05
Patent number
US06737437B2

Reaction notes

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