4-Phenylpiperidine → 1-{[(3S,4S)-1-Benzyl-4-phenyl-3-pyrrolidinyl]methyl}-4-phenylpiperidine

HRID 1276508Notes

Reaction equation

HRID 1276508 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH:19]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[C:2]1([CH2:1][N:8]2[CH2:12][C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@@H:10]([CH2:19][N:30]3[CH2:31][CH2:32][CH:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:28][CH2:29]3)[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 698734-PhenylpiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 54388031(3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carbaldehyde

Product 1

HCID 4563741-{[(3S,4S)-1-Benzyl-4-phenyl-3-pyrrolidinyl]methyl}-4-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2.68 g (10 mmol) of 1-benzyl-3-(R)-formyl-4-(S)-phenylpyrrolidine in 10 mL of 1,2-dichlorethane was added 2.0 g (12 mmol) of 4-phenylpiperidine. To this was added 3.2 g (15 mmol) of sodium triacetoxyborohydride and the solution was stirred at room temperature for 1 h. The reaction was poured into 50 mL of saturated NaHCO3 solution and the mixture was extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel using ethyl acetate-hexane (1:1) to afford the title compound. 1H NMR (CDCl3) δ 1.6-1.85 (m, 4H), 1.98 (dq, J=7 Hz, J=2 Hz, 2H), 2.4-2.56 (m, 4H), 2.62 (m, 1H), 2.72 (m, 1H), 2.83 (m, 1H), 3.04 (m, 4H), 3.69 (d, AB, J=7 Hz, 1H), 3.77 (d, AB, J=7 Hz, 1H), 7.2-7.6 (m, 15H); Mass Spectrum (ESI) m/e 411 (M+1); [α]D =+26.0 (c.=1.56, CHCl3)

Workup

  1. extractionthe mixture was extracted with three portions of ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e430b9bbda26491882ffec941cdc77bd
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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