tert-Butyldimethylsilyl chloride → 5-[3-(Tert-butyl-dimethyl-silanyloxy)4-(3-chloro-phenyl)-butyl]-pyrrolidin-2-one

HRID 458973Notes

Reaction equation

HRID 458973 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:18])[CH2:10][CH2:11][CH:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][CH:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:10][CH2:11][CH:12]1[NH:16][C:15](=[O:17])[CH2:14][CH2:13]1)([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 129700915-[4-(3-Chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one

Product 1

HCID 129701005-[3-(Tert-butyl-dimethyl-silanyloxy)4-(3-chloro-phenyl)-butyl]-pyrrolidin-2-oneYield 81.1%

Procedure

Analogous to the procedure described for Example 1A, Step C, 5-[4-(3-chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (1.53 g, 5.71 mmol) was reacted with tert-butyldimethylsilyl chloride (0.97 g, 6.4 mmol). Purification by medium pressure chromatography using a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2) provided 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-chloro-phenyl)-butyl]-pyrrolidin-2-one (1.77 g). 1H NMR (CDCl3) δ7.16 (m, 3H), 7.01 (m, 1H), 5.61 (d, 1H), 3.83 (m, 1H), 3.58 (m, 1H), 2.68 (m, 2H), 2.28 (m, 3H), 1.73–1.36 (m, 5H), 0.84 (s, 9H), −0.05 (s, 3H), −0.2 (d, 3H).

Workup

  1. customPurification by medium pressure chromatography

Sources & evidence

ORD record
ord-f250d922c2e64c2db0caf43aee1be658
Source dataset
uspto-grants-2007_03
Patent number
US07192979B2

Reaction notes

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