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

HRID 478862Notes

Reaction equation

HRID 478862 reaction equation
[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([O:25][Si](C(C)(C)C)(C)C)[CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][C:13](=[O:16])[N:12]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[C:1]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([OH:25])[CH2:9][CH2:10][CH:11]2[CH2:15][CH2:14][C:13](=[O:16])[N:12]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH:2]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 227187667-{2-[4-Biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

Product 1

HCID 227187617-[2-(4-Biphenyl-3-yl-3-hydroxy-butyl)-5-oxo-pyrrolidin-1-yl]-heptanenitrileYield 57.9%

Procedure

Following the procedure described for Example 5, Step B, 7-{2-[4-biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (187 mg, 0.351 mmol) was deprotected with TBAF (1M in THF, 0.53 mL, 0.53 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 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2) provided 7-[2-(4-biphenyl-3-yl-3-hydroxy-butyl)-5-oxo-pyrrolidin-1-yl ]-heptanenitrile (85 mg). 1H NMR (CDCl3) δ7.58 (m, 1H), 7.51-7.33 (m, 4H), 7.21-7.12 (m, 4H), 3.85 (m, 1H), 3.60 (m, 2H), 2.90 (m, 1H), 2.83-2.60 (m, 2H), 2.45-2.30 (m, 4H), 2.14 (m, 1H), 1.73-1.25 (m, 14H).

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 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-eb8de192305345d5bf4e65633c71f48f
Source dataset
uspto-grants-2003_11
Patent number
US06642266B2

Reaction notes

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