Benzyl ethyl(piperidin-4-yl)carbamate → benzyl ethyl{1-[((1S,2S)-2-{[methyl(phenylsulfonyl)amino]methyl}-2-phenylcyclopropyl)methyl]piperidin-4-yl}carbamate
Reaction equation
[CH:1]([C@H:3]1[CH2:5][C@@:4]1([CH2:12][N:13]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH2:24]([N:26]([CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:25]>>[CH2:24]([N:26]([CH:37]1[CH2:42][CH2:41][N:40]([CH2:1][C@H:3]2[CH2:5][C@@:4]2([CH2:12][N:13]([CH3:23])[S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:39][CH2:38]1)[C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:25]Participants
3
Procedure
N-{[(1S,2S)-2-formyl-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide and benzyl ethyl(piperidin-4-yl)carbamate (incorporating by reference as needed Bioorg. and Med. Chem. Lett., 11 (2001), 2475) were reacted as per Preparation 10 to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.67-7.55 (m, 5H), 7.39-7.21 (m, 10H), 5.07 (s, 2H), 3.67 (m, 1H), 3.57 (d, J=13.3 Hz, 1H), 3.17 (q, J=6.6 Hz, 2H), 2.99-2.93 (m, 1H), 2.76 (d, J=13.3 Hz, 1H), 2.75-2.68 (m, 1H), 2.52 (s, 3H), 2.29-2.19 (m, 1H), 1.87-1.38 (m, 7H), 1.11 (m, 1H), 1.04 (t, J=6.6 Hz, 3H), 1.07-1.03 (m, 1H), 0.90 (m, 1H). ES-LCMS m/z 576.2 (M+H).
Sources & evidence
- ORD record
- ord-e5601a9b11ea44e38048e9e04aa61799
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569579B2
Reaction notes
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