Acetonitrile → HCID 18423463, compound

HRID 1281995Notes

Reaction equation

HRID 1281995 reaction equation
C([N:4]1[CH2:8][CH:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:6]([CH2:14][OH:15])[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>[OH:15][CH2:14][CH:6]1[CH:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH2:8][NH:4][CH2:5]1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 18374741HCID 18374741, compound

Product 1

HCID 18423463HCID 18423463, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

A mixture of 3.5 g (15.7 mmol) of 1-allyl-3-(SR)-hydroxymethyl-4-(RS)-(3-thienyl)pyrrolidine and 400 mg (0.43 mmol) of Wilkinson's catalyst [Rh(PPh3)3Cl] in 200 mL of an 85% solution of CH3CN and water was heated to 90° C. and stirred for 3 h. The reaction mixture was cooled to rt and concentrated to give the title compound which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2d3c2b7a74fa4c208c2cf4b3ba712bc3
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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