Acetonitrile → 3-(RS)-(4-(4-Fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

HRID 279216Notes

Reaction equation

HRID 279216 reaction equation
C([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:5]1)C=C.CC#N>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH:6]3[CH:7]([CH:9]4[CH2:10][CH2:11]4)[CH2:8][NH:4][CH2:5]3)[CH2:14][CH2:15]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 226244721-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Product 1

HCID 226244713-(RS)-(4-(4-Fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 962WaterSolvent

Procedure

A mixture of 0.2 g (0.58 mmol) of 1-allyl-3-(RS)-(4-(4-fluoro phenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine and 0.02 g (0.02 mmol) of Wilkinson's catalyst [Rh(PPh)3Cl] in 10 mL of an 90% solution of CH3CN and water in a Dean-Stark apparatus was heated at reflux and stirred for 3 h. The reaction mixture was cooled to rt and concentrated. The residue was purified by chomatography (silica, CHCl3: MeOH: NH3, 90: 10:1) to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationconcentrated
  4. customThe residue was purified by chomatography (silica, CHCl3: MeOH: NH3, 90: 10:1)

Sources & evidence

ORD record
ord-6aac1c92b9ae4654845ddabd7a34de9c
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

Loading…