Heptanenitrile, 7-bromo- → 7-{2-[4-Biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile

HRID 1582662Notes

Reaction equation

HRID 1582662 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:9][CH2:10][CH:11]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12]2)[CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]#[N:49]>>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13][C:14](=[O:16])[N:15]2[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]#[N:49])[CH:2]=1

Participants

4

Reactant 3

HCID 88737Heptanenitrile, 7-bromo-HCID 2724254Sodium bis(trimethylsilyl)amideHCID 227124795-[4-Biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-one

Product 1

HCID 227187667-{2-[4-Biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrileYield 62.2%

Procedure

Following the procedure described for Example 5, Step A, the anion derived from 5-[4-biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-one (239.1 mg, 0.564 mmol) and NaHMDS (1M in THF, 0.67 mL, 0.67 mmol) was alkylated with 7-bromoheptanenitrile (118 mg, 0.620 mmol) at 70° C. 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-biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (187 mg). MS 533.3 (M+1).

Workup

  1. 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-44fc4ddb2e36441896e00a3646c6de47
Source dataset
uspto-grants-2004_05
Patent number
US06737437B2

Reaction notes

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