Water → HCID 57618621, compound

HRID 553421Notes

Reaction equation

HRID 553421 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]2[CH2:11][N:12]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:14][C:9]2(N2CCCC2)[O:8][N:7]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O.O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][N:12]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 576186195-Acetyl-7a-pyrrolidin-1-yl-3a,4,5,6,7,7a-hexahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester

Product 1

HCID 57618621HCID 57618621, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 18.0 g (58 mmol) of 5-acetyl-7a-pyrrolidin-1-yl-3a,4,5,6,7,7a-hexahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester (B) in 150 mL of DCM and 6.47 mL (87 mmol) of trifluoroacetic acid was heated to reflux for 8 h. After addition of 100 mL of water, the organic phase was dried over MgSO4 and the solvent removed under a vacuum. The remaining brown oil was purified by column chromatography (SiO2, EtOAc/EtOH 10:1). 12.5 g (90% of theoretical) of the desired product 5-acetyl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester (C) were obtained in the form of a brown-yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. dry with materialthe organic phase was dried over MgSO4
  4. customthe solvent removed under a vacuum
  5. customThe remaining brown oil was purified by column chromatography (SiO2, EtOAc/EtOH 10:1)

Sources & evidence

ORD record
ord-1345c9612dcd45efb79401cc3bce7f0b
Source dataset
uspto-grants-2011_11
Patent number
US08048879B2

Reaction notes

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