Diisopropylethylamine → (2R,5R)-2-(2,2-Dimethylpropoxy)-5-formylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20407

Reaction equation

HRID 20407 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][OH:15])[CH2:12][O:11][C@@H:10]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C>CS(C)=O.ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C@@H:10]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 68564170(2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 86615359(2R,5R)-2-(2,2-Dimethylpropoxy)-5-formylmorpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Add pyridine sulfur trioxide complex (4.82 g, 30.26 mmol) to (2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (5.10 g, 16.81 mmol) and N,N-diisopropylethylamine (7.61 g, 58.83 mmol) in dimethylsulfoxide (42 mL) and dichloromethane (8 mL) at −4° C. Stir 20 minutes, pour into ice cold saturated aqueous sodium chloride. Extract with 10% ethyl acetate/hexanes. Wash with 0.1 N aqueous citric-acid and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate to give the desired compound of a colorless oil, which is used directly in the next step without further purification (5.02 g).

Workup

  1. additionpour into ice cold saturated aqueous sodium chloride
  2. extractionExtract with 10% ethyl acetate/hexanes
  3. washWash with 0.1 N aqueous citric-acid and saturated aqueous sodium chloride
  4. dry with materialDry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-dd21696450dd4e3db86f17bc2b47576e
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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