Water → 2-(S)-(2-Cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20369Notes

Reaction equation

HRID 20369 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]([CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O>CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C@@H:10]([CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 685596732-(S)-(2-Cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 866153612-(S)-(2-Cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

Dissolve 2-(S)-(2-cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (165 mg, 0.50 mmol) in dimethylsulfoxide (2 mL), and cool to 10° C. Add triethylamine (0.28 mL, 2.02 mmol) followed by pyridine sulfur trioxide complex and stir for 30 min. Dilute with ethyl acetate and pour into cold water. Wash with 5% citric acid (50 mL), saturated aqueous sodium chloride (50 mL) and dry (sodium sulfate), filter and concentrate give the desired compound as an oil which is used without further purification.

Workup

  1. washWash with 5% citric acid (50 mL), saturated aqueous sodium chloride (50 mL)
  2. dry with materialdry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-2ba6262a95b94b529d2492702735d006
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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