Piperidin-4-ol → 1-Benzyl-3-(SR)-(4-hydroxypiperidin-1-ylmethyl)-4-(SR)-phenyl-pyrrolidine

HRID 1276491Notes

Reaction equation

HRID 1276491 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.[OH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]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:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([CH2:19][N:25]2[CH2:26][CH2:27][CH:22]([OH:21])[CH2:23][CH2:24]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 79341Piperidin-4-olHCID 5049666Sodium triacetoxyborohydrideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine

Product 1

HCID 702003791-Benzyl-3-(SR)-(4-hydroxypiperidin-1-ylmethyl)-4-(SR)-phenyl-pyrrolidineYield 52.7%

Procedure

The title compound was prepared from 500 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 196 mg of 4-hydroxypiperidine and 597 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 348 mg of the title compound. RF : 0.16 (5% MeOH in CH2Cl3). 1H NMR (300 MHz, CDCl3): δ1.35-1.54 (m, 2H), 1.69-1.83 (m, 2H), 1.93-2.05 (m, 2H), 2.36-2.71 (m, 7H), 3.89-3.01 (m, 3H), 3.55-3.72 (m, 3H), 7.14-7.38 (m, 10H). Mass Spectrum (NH3 -CI): 351.3 (M+H).

Sources & evidence

ORD record
ord-39c0c5b1c79d4eb29542c6fa406a51af
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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