HCID 68158227, compound → 1392811-96-9

HRID 1950764Notes

Reaction equation

HRID 1950764 reaction equation
C[O:2][CH:3](OC)[C:4]1[C@H:8]2[CH2:9][O:10][CH2:11][C@H:7]2[O:6][N:5]=1>FC(F)(F)C(O)=O.O>[O:6]1[C@@H:7]2[CH2:11][O:10][CH2:9][C@@H:8]2[C:4]([CH:3]=[O:2])=[N:5]1

Participants

4

Reactant 1

HCID 68158227HCID 68158227, compound

Product 1

HCID 888515491392811-96-9Yield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (3aS,6aS)-rel-3-dimethoxymethyl-3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazole (35.3 mmol) in trifluoroacetic acid (30 ml) was treated with water (1.3 ml). The mixture was stirred at room temperature for 30 minutes. For the workup, the reaction mixture was diluted with water (100 ml) and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulphate and evaporated. The crude product was purified by chromatography on silica gel using a 5:1-mixture of dichloromethane and heptane as the eluent. The (3aS,6aS)-rel-3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazole-3-carbaldehyde (4.79 g, 96% yield) was obtained as a yellow oil. MS: m/z=144.0 [M+H]+.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated
  4. customThe crude product was purified by chromatography on silica gel using a 5

Sources & evidence

ORD record
ord-437633aca92b49149d2b420fd225b27b
Source dataset
uspto-grants-2013_03
Patent number
US08404680B2

Reaction notes

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