Triphenylphosphine → HCID 66594811, compound

HRID 1091373Notes

Reaction equation

HRID 1091373 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:27][CH2:26][CH2:25][N:24]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:23]2)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:54]([N:57]1[CH2:62][CH2:61][CH:60](O)[CH2:59][CH2:58]1)(=[O:56])[CH3:55]>O1CCCC1>[C:54]([N:57]1[CH2:62][CH2:61][CH:60]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C@@H:22]3[O:27][CH2:26][CH2:25][N:24]([CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:23]3)=[CH:20][CH:21]=2)[CH2:59][CH2:58]1)(=[O:56])[CH3:55]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-oneHCID 66594479HCID 66594479, compound

Product 1

HCID 66594811HCID 66594811, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (40% in toluene, 5.7 g, 11.3 mmol) was added to a solution of (2S)-2-(4-hydroxyphenyl)-4-benzylmorpholine (2.0 g, 7.43 mmol), triphenylphosphine (3.0 g, 11.4 mmol) and 1-acetyl-4-hydroxypiperidin (1.6 g, 11.2 mmol) in tetrahydrofuran (40 ml) at room temperature and the mixture stirred for 10 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography eluting 10-50% ethyl acetate in hexane to furnish (2S)-2-(4-(1-acetylpiperidin-4-yloxy)phenyl)-4-benzylmorpholine (1.68 g, 57%) as colorless oil.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting 10-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2aaafb3a423c4499b3a54c5d2a7f97cc
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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