Potassium bisulfate → (R)-Benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate

HRID 1876239Notes

Reaction equation

HRID 1876239 reaction equation
CON(C)[C:4]([C@H:6]1[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:5].OS([O-])(=O)=O.[K+]>C1COCC1>[CH:4]([C@H:6]1[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])=[O:5]

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 11278709HCID 11278709, compound

Product 1

HCID 11414364(R)-Benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiALH4 (1 M, 20 mL, 20 mmol) was added dropwise to a cold (−15° C.) solution of (R)-benzyl 4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate (12.2 g, 37.9 mmol) in THF (75 mL). The mixture was stirred for 30 min keeping the temperature below 0° C. A saturated solution of KHSO4 (100 mL) was added slowly to the mixture and it was warmed to room temperature. The mixture was filtered and the solvent was removed to dryness. (R)-benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate was obtained as a clear oil (9.161 g, 92% yield) after purification by column chromatography (SiO2, using a mixture of hexane/EtOAc). 1H NMR (CDCl3, 400 mHz, ppm); 1.7 (m, 6H), 4.15 (m, 2H), 4.4 (m, 1H), 5.15, (s, 1H), 5.2 (m, 1H), 7.3 (m, 5H), 9.6 (m, 1H).

Workup

  1. customthe temperature below 0° C
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed to dryness

Sources & evidence

ORD record
ord-7ec26931123549f19957154e82bd27cb
Source dataset
uspto-grants-2012_11
Patent number
US08309593B2

Reaction notes

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