benzyl[2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)hexahydro-2,5-methanopentalene-3a(1H)-yl]carbamate → 1-[4-(1,1-Dioxidoisothiazolidin-2-yl) phenyl]tricyclo[3.3.1.03,7]nonan-3-amine
Reaction equation
C(OC(=O)[NH:10][C:11]12[CH2:18][CH:17]3[CH2:19][C:13]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:30][CH2:29][CH2:28][S:27]5(=[O:32])=[O:31])=[CH:22][CH:21]=4)([CH2:14][CH:15]1[CH2:16]3)[CH2:12]2)C1C=CC=CC=1>CO.[Pd]>[O:31]=[S:27]1(=[O:32])[CH2:28][CH2:29][CH2:30][N:26]1[C:23]1[CH:22]=[CH:21][C:20]([C:13]23[CH2:19][CH:17]4[CH2:16][CH:15]([CH2:14]2)[C:11]([NH2:10])([CH2:18]4)[CH2:12]3)=[CH:25][CH:24]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of benzyl[2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)hexahydro-2,5-methanopentalene-3a(1H)-yl]carbamate (0.8 g, 1.7 mmol) obtained in step I, Pd/C (10%, 0.4 g) in MeOH (17 mL) was stirred at room temperature under H2 atmosphere for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to obtain 1-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]tricyclo[3.3.1.03,7]nonan-3-amine as an off-white solid (0.49 g) in 85% yield. m/z (M+1) 333; IR cm−1 3418, 1652, 1137, 772. 1H NMR (CDCl3) 300 MHz, δ 7.31 (d, J=8.8 Hz, 2H), 7.22 (d, J=8.8 Hz, 2H), 3.78 (t, J=6.6 Hz, 2H), 3.43 (t, J=7.4 Hz, 2H), 2.58-2.47 (m, 3H), 2.40-2.34 (m, 1H), 2.27-2.11 (m, 2H), 2.10-1.95 (m, 4H), 1.93-1.70 (m, 4H).
Workup
- filtrationThe reaction mixture was filtered through a pad of celite
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d725f5ea2f594d4ea184ef94284138e9
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985759B2
Reaction notes
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