tert-Butyldimethylsilyl chloride → HCID 22712496, compound

HRID 2219692Notes

Reaction equation

HRID 2219692 reaction equation
[OH:1][CH:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>>[C:28]([Si:25]([CH3:27])([CH3:26])[O:1][CH:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1)([CH3:31])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 22712501HCID 22712501, compound

Product 1

HCID 22712496HCID 22712496, compoundYield 74.7%

Procedure

Analogous to the procedure described for Compound 1A, Step C, 5-[3-hydroxy-4-(3-phenoxy-phenyl)-butyl]-pyrrolidin-2-one (668.3 mg, 2.05 mmol) was reacted with tert-butyldimethylsilyl chloride (341 mg, 2.26 mmol). Purification by medium pressure chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% MeOH in CH2Cl2) provided 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-phenoxy-phenyl)-butyl]-pyrrolidin-2-one (673 mg). 1H NMR (CDCl3) δ 7.32 (m, 2H), 7.22 (m, 1H), 7.09 (m, 1H), 6.99 (d, 2H), 6.89 (d, 1H), 6.83 (m, 2H), 3.85 (m, 1H), 3.58 (m, 1H), 2.76-2.62 (m, 2H), 2.32 (m, 2H), 2.23 (m, 1H), 1.73-1.34 (m, 5H), 0.84 (s, 9H), −0.03 (d, 3H), −0.16 (d, 3H); MS 440.7 (M+1).

Workup

  1. customPurification by medium pressure chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9c5b5983522345f8ac590423df377a42
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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