Water → 3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-

HRID 20419

Reaction equation

HRID 20419 reaction equation
S(=O)(=O)=O.N1C=CC=CC=1.[C:11]([O:15][C:16]([N:18]1[C@@H:22]([CH2:23][OH:24])[CH2:21][O:20][C:19]1([CH3:26])[CH3:25])=[O:17])([CH3:14])([CH3:13])[CH3:12].O>CS(C)=O.C(N(C(C)C)CC)(C)C>[C:11]([O:15][C:16]([N:18]1[C@H:22]([CH:23]=[O:24])[CH2:21][O:20][C:19]1([CH3:26])[CH3:25])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 168533Sulfur trioxide-pyridineHCID 11053463(S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
15 °C

Procedure

Add dropwise over 2 hours a solution of pyridine sulfur trioxide (390 g, 2452.83 mmol) in dimethylsulfoxide (1600 mL) to a 6° C. maintained solution of (S)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (350 g, 1515.15 mmol) in diisopropylethylamine (1225 mL) with a dimethylsulfide trap. Over 30 minutes add water (1050 mL) keeping temperature below 15° C. Stir at 15° C. for 1.5 hours under a stream of nitrogen. Extract with ethyl acetate (5 L), wash with 5%-aqueous citric acid (2×1.5 L), saturated aqueous sodium chloride (2×1.5 L), dry (magnesium sulfate), filter, and concentrate to give the desired compound which is used in the next reaction without further purification (365 g).

Workup

  1. customtemperature below 15° C
  2. extractionExtract with ethyl acetate (5 L)
  3. washwash with 5%-aqueous citric acid (2×1.5 L), saturated aqueous sodium chloride (2×1.5 L)
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-aa9a42206f8c40a29cad1f733ff1dfa1
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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