Diisopropylethylamine → 1-Benzyl-3-(SR)-(4-(2-tolyl)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

HRID 1276494Notes

Reaction equation

HRID 1276494 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([CH3:34])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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[CH2:32][CH2:33][CH:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH3:34])[CH2:29][CH2:30]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 219369564-(2-Methylphenyl)piperidine hydrochlorideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine

Product 1

HCID 701994401-Benzyl-3-(SR)-(4-(2-tolyl)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidineYield 84.1%

Procedure

The title compound was prepared from 21 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 16 mg of 4-(2-tolyl)-piperidine-hydrochloride, 0.013 mL of DIEA and 23 mg of sodium triacetoxy-borohydride using a procedure analogous to that described in Example 9, Step B to provide 27 mg of the title compound. HPLC (YMC "Octyl" 4.6×250 mm column, 60:40 v/v H2O/CH3CN+0.5% TFA, 1.5 mL/min, 200 nm): Retention Time: 6.69 min. 1H NMR (300 MHz, CDCl3): δ1.58-1.74 (m, 6H), 1.91-1.99 (m, 2H), 2.28 (s, 3H), 2.47-2.82 (m, 6H), 2.98-3.00 (m, 3H), 3.70 (ABq, J=13 Hz, 2H), 7.04-7.40 (m, 14H). Mass Spectrum (ESI): 425.2 (M+H).

Sources & evidence

ORD record
ord-a598cbf386d540119d64ae15aea3a247
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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