Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate → 3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (A+-)-

HRID 227567Notes

Reaction equation

HRID 227567 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH:13]=[O:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14409442Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 36440903-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (A+-)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (36) (80 mg, 0.346 mmol) stirring in CH2Cl2 (2 mL), under a nitrogen atmosphere, was added pyridinium chlorochromate (150 mg, 0.694 mmol). The reaction mixture was allowed to stir overnight then filtered through a plug of silica gel. The crude aldehyde was carried on to the following step.

Workup

  1. filtrationthen filtered through a plug of silica gel

Sources & evidence

ORD record
ord-00992d449fab45faba4bc0d2acb51e0f
Source dataset
uspto-grants-2009_07
Patent number
US07560477B2

Reaction notes

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