(S)-5-benzyloxymethyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester → (R)-5-Formyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20396Notes

Reaction equation

HRID 20396 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][O:15]CC2C=CC=CC=2)[CH2:12][O:11][C:10]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C:10]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68561079(S)-5-benzyloxymethyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86615365(R)-5-Formyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To 10% palladium on carbon (2.1 g) in ethanol (50 mL) add (S)-5-benzyloxymethyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester (3.29 g, 7.16 mmol) in ethanol (75 mL) and stir under 1 atmosphere of hydrogen gas at room temperature for 4 hours. Filter and concentrate to give the desired compound as a white solid. Dissolve the solid in dimethylsulfoxide (20 mL) and add triethylamine (1.30 g, 12.82 mmol), then pyridine sulfur trioxide complex (1.84 g, 11.55 mmol). Stir at room temperature 3 hours and dilute with 10% ethyl acetate/hexanes (˜150 mL). Wash with water, 1 N aqueous citric acid and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to give the desired compound as a white solid.

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-dff332a6a8d240d9bc709087f7d05a66
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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