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

HRID 919024Notes

Reaction equation

HRID 919024 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).

Workup

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

Sources & evidence

ORD record
ord-1c1c01bf4d184c7cb37b4fa5ed48c8e7
Source dataset
uspto-grants-2016_03
Patent number
US09272996B2

Reaction notes

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