Benzyl Bromide → 3-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

HRID 458153Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][NH:13][C:12]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[H-].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:12]2=[O:22])[CH2:23][CH2:24]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 7498Benzyl Bromide

HCID 24758Sodium hydride

HCID 389488tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 223806103-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

Procedure

The title compound was prepared from 4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (J. Med. Chem. (1992), 35, 423–30) and benzylbromide in analogy of the procedure described for the synthesis of (rac,cis)-3-methyl-1-phenyl-8-(2-phenyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]decan-4-one (Example 69) by using potassium bis(trimethylsilyl)amide as base instead of sodium hydride. 3-Benzyl-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester was obtained as colorless solid; MS (ISP): 322.6 [M-(CO2+isobutylene)]+.

Sources & evidence

ORD record: ord-7b91b2c6d42049b595b338c5990517c3
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189850B2

Reaction notes

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