1,2,3,4-Tetrahydroisoquinoline → 1-Benzyl-3-(SR)-(1, 2, 3, 4-tetrahydroisoquinolin-2-ylmethyl)-4-(SR)-phenylpyrrolidine
Reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH:19]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][NH:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:22]2[CH2:23][CH2:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
The title compound was prepared from 20 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 0.010 mL of 1, 2, 3, 4-tetrahydro-isoquinoline and 25 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 25 mg of the title compound. RF : 0.51 (50% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3): δ2.51-2.78 (m, 9H), 2.94-3.00 (m, 3H), 3.40-3.69 (m, 4H), 6.91-6.94 (m, 1H ), 7.02-7.38 (m, 13H). Mass spec. (ESI): 383.2 (M+H).
Sources & evidence
- ORD record
- ord-0d548091822b43149e314c2442935a5a
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06166037
Reaction notes
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