Triphenylphosphine → HCID 86760815, compound

HRID 1725757Notes

Reaction equation

HRID 1725757 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][CH:7]1[C:11](=C)[CH2:10][CH2:9][C:8]1([CH:16]([CH3:18])[CH3:17])[C:13]([NH2:15])=[O:14].[O:28]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:24][C:22]([F:23])([F:25])[C:20]1[CH:19]=[C:5]([CH:4]=[C:3]([C:2]([F:26])([F:27])[F:1])[CH:21]=1)[CH2:6][CH:7]1[C:11](=[O:28])[CH2:10][CH2:9][C:8]1([CH:16]([CH3:18])[CH3:17])[C:13]([NH2:15])=[O:14]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 86760814HCID 86760814, compound

Product 1

HCID 86760815HCID 86760815, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,5-bis(trifluoromethyl)benzyl 3-methylene-1-isopropylcyclopentane-carboxamide (910 mg, 2.31 mmol) in dichloromethane (50 mL) was cooled to −78° C. and a stream of ozone was passed through until the permanent blue color indicated complete consumption of the olefin. The excess ozone was purged with a stream of nitrogen, and triphenylphosphine (729 mg, 2.78 mmol) was added. The cooling bath was removed, and the reaction mixture was allowed to stir at ambient temperature overnight. The solvent was removed in vacuo, the residue was purified by column chromatography (silica gel, ethyl acetate:hexane/1:2) to give 760.7 mg (83%) of the desired product. 1H NMR (500 MHz, CDCl3): 7.81 (s, 1H), 7.74 (s, 2H), 6.16 (bs, 1H), 6.61 (m, 2H), 2.78 (bd, J=18.07 Hz, 1H), 2.40 to 2.20 (bm, 4H), 2.08-1.98 (m, 2H), 0.99 (d, J=6.86 Hz, 3H), 0.97 (d, J=6.87 Hz, 3H).

Workup

  1. customconsumption of the olefin
  2. additionwas added
  3. customThe cooling bath was removed
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography (silica gel, ethyl acetate:hexane/1:2)

Sources & evidence

ORD record
ord-06c587d4a6a242a69a7fb5c54d646fe3
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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