Triphenylphosphine → HCID 44308832, compound

HRID 369905Notes

Reaction equation

HRID 369905 reaction equation
[N:1]([CH2:4][CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:28])[C@:13]([C@@H:21]2[CH2:25][CH2:24][C:23]([F:27])([F:26])[CH2:22]2)([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH2:4][CH:5]=[C:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:28])[C@:13]([C@@H:21]2[CH2:25][CH2:24][C:23]([F:26])([F:27])[CH2:22]2)([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 54121281HCID 54121281, compound

Product 1

HCID 44308832HCID 44308832, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 18 mg of 4-(2-azidoethylidene)-1-{(2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetyl}piperidine in 2.2 ml of 10% aqueous tetrahydrofuran, 15 mg of triphenylphosphine was added at room temperature, followed by reflux for 15 hours under heating. The solvent was distilled off under reduced pressure, and 15 mg of the title compound was obtained as a colorless oily substance by purifying the resulting residue by preparative thin-layer chromatography [Kieselgel™60F654, Art 5744 (Merck); chloroform/methanol/aqueous ammonia=20/1].

Workup

  1. temperatureby reflux for 15 hours
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-03621006772c42a5a53b261d3e2a4f76
Source dataset
uspto-grants-2000_10
Patent number
US06140333

Reaction notes

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