Triphenylphosphine → HCID 68479666, compound

HRID 2191123Notes

Reaction equation

HRID 2191123 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH:10]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[CH:27][C:28](O)=[N:29][CH:30]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:28]2[CH:27]=[CH:26][C:25]([Cl:24])=[CH:30][N:29]=2)[CH:10]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 68473945HCID 68473945, compoundHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 68479666HCID 68479666, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 g (3 mmol) (3SR,4SR)-3-(3,4-Difluoro-phenyl)-4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester, 0.59 g (4.5 mmol) 5-chloro-2-hydroxy pyridine, 1.1 g (4.8 mmol) di-tert-butyl azodicarboxylate and 2.42 g (5 mmol) triphenylphosphine (polymer bound) in 70 mL THF was stirred at room temperature over night. the mixture was filtered through decalite and evaporated to dryness. The residue was subjected to column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to afford after evaporation of the product containing fractions 1.2 g (91%) of the title compound as viscous colorless oil. MS (m/e): 439.1 [(M+H)+].

Workup

  1. filtrationthe mixture was filtered through decalite
  2. customevaporated to dryness
  3. customformed from ethyl acetate and heptane
  4. customto afford
  5. customafter evaporation of the product
  6. additioncontaining fractions 1.2 g (91%) of the title compound as viscous colorless oil

Sources & evidence

ORD record
ord-eec7e90d835e48b0aba644a3c6d40f45
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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