Triphenylphosphine → HCID 68523774, compound

HRID 2246740Notes

Reaction equation

HRID 2246740 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[Cl:13][CH2:14][CH2:15][C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:13][CH2:14][CH2:15][C@@H:16]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:12])([CH3:1])[C:3]1=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

Product 1

HCID 68523774HCID 68523774, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3,3-dimethyloxindole (409 mg, 2.53 mmol), (S)-3-chloro-1-phenyl-1-propanol (376 mg, 2.20 mmol) and triphenylphosphine (664 mg, 2.53 mmol) in tetrahydrofuran (5 mL) under nitrogen was added slowly diisopropyl azodicarboxylate (490 μL, 2.53 mmol) via a syringe. The resulting solution was stirred at room temperature overnight. Solvent was removed under reduced pressure and the viscous brown liquid residue was purified using Isco CombiFlash Companion chromatography (RediSep 12-g silica column, 0-12% ethyl acetate/hexane) to give 236 mg (34%) of 1-[(1R)-3-chloro-1-phenylpropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a viscous colorless liquid. MS (ES) m/z 314.1 ([M+H]+); HRMS: calculated for C19H20ClNO+H+, 314.1306; found (ESI, [M+H]+), 314.1299.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe viscous brown liquid residue was purified

Sources & evidence

ORD record
ord-191b7f30b2924bdfa310f8ab19ed8c27
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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