Diisopropylethylamine → 1-Benzyl-3-(SR)-(4-phenyl-1, 2, 3, 6-tetrahydropyridin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

HRID 1276495Notes

Reaction equation

HRID 1276495 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.Cl.[C:22]1([C:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C.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:31]2[CH2:30][CH:29]=[C:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:33][CH2:32]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27238604-Phenyl-1,2,3,6-tetrahydropyridine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine

Product 1

HCID 702728631-Benzyl-3-(SR)-(4-phenyl-1, 2, 3, 6-tetrahydropyridin-1-ylmethyl)-4-(SR)-phenylpyrrolidineYield 77.9%

Procedure

The title compound was prepared from 20 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 16 mg of 4-phenyl-1, 2, 3, 6-tetrahydropyridine-hydrochloride, 0.013 mL of DIEA and 23 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 24 mg of the title compound. RF: 0.37 (50% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3): δ2.40-2.71 (m, 9H), 2.91-3.16 (m, 5H), 3.67 (ABq, J=13 Hz, 2H), 5.98-6.00 (m, 1H ), 7.07-7.41 (m, 15H). Mass Spectrum (ESI): 409.1 (M+H).

Sources & evidence

ORD record
ord-6f8133fae533458190ca0bf5fafc8f3c
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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