Benzyl ethyl(piperidin-4-yl)carbamate → Benzyl ethyl{1-[((1R,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,2R)-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-d8) δ 7.70-7.56 (m, 5H), 7.40-7.17 (m, 10H), 5.09 (s, 2H), 3.88 (d, J=13.3 Hz, 1H), 3.75 (m, 1H), 3.19 (q, J=6.6 Hz, 2H), 3.09-3.05 (m, 1H), 2.91-2.87 (m, 1H), 2.83 (d, J=13.3 Hz, 1H), 2.58-2.52 (m, 1H), 2.52 (s, 3H), 2.44-2.38 (m, 1H), 2.08-1.92 (m, 2H), 1.77-1.58 (m, 4H), 1.41-1.37 (m, 0.1H), 1.07 (t, J=6.6 Hz, 3H), 1.07-0.99 (m, 1H), 0.78 (m, 1H). ES-LCMS m/z 576.1 (M+H).
Sources & evidence
- ORD record
- ord-049df038e6624b1cb8c8c2cb1f0f1577
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569579B2
Reaction notes
Loading…