1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → tert-Butyl (1-{[3-(4-ethylphenyl)-5-(phenylcarbamoyl)piperidin-1-yl]carbonyl}cyclopropyl)carbamate

HRID 876270Notes

Reaction equation

HRID 876270 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].[C:24]([O:28][C:29]([NH:31][C:32]1([C:35](O)=[O:36])[CH2:34][CH2:33]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH:11]([C:15](=[O:16])[NH:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][N:13]([C:35]([C:32]3([NH:31][C:29](=[O:30])[O:28][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:34][CH2:33]3)=[O:36])[CH2:14]2)=[CH:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 667015535-(4-ethylphenyl)-N-phenylpiperidine-3-carboxamide

Product 1

HCID 70854693tert-Butyl (1-{[3-(4-ethylphenyl)-5-(phenylcarbamoyl)piperidin-1-yl]carbonyl}cyclopropyl)carbamate

Procedure

169 mg (0.50 mmol) of 5-(4-ethylphenyl)-N-phenylpiperidine-3-carboxamide (Example 17A) and 111 mg (0.55 mmol, 1.1 eq.) of 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylic acid were reacted according to General Method 1. Yield: 119 mg (48% of theory)

Sources & evidence

ORD record
ord-95888960c2a14dfb9a488cfe02ae5de4
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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