Potassium Carbonate → tert-Butyl (1R,6S)-3,8-diazabicyclo[4.2.0]octane-8-carboxylate

HRID 747913Notes

Reaction equation

HRID 747913 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:15]2[C@@H:10]([CH2:11][CH2:12][N:13](C(=O)C(F)(F)F)[CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.O.[NH4+].[OH-]>[C:1]([O:5][C:6]([N:8]1[C@@H:15]2[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 86624420(1R,6S)-3-(2,2,2-Trifluoro-acetyl)-3,8-diaza-bicyclo[4.2.0]octane-8-carboxylic acid tert-butyl ester

Product 1

HCID 16099058tert-Butyl (1R,6S)-3,8-diazabicyclo[4.2.0]octane-8-carboxylateYield 55.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To the crude product of Example 3H (˜28.2 mmol) in 140 mL CH3OH and 30 mL H2O was added 4.7 g K2CO3 (33.8 mmol). The mixture stirred at ambient temperature for 16 h then was diluted with a 100 mL of a solution of 1% NH4OH: 9% CH3OH: 90% CH2Cl2 and filtered through Celite® diatomaceous earth and silica gel. The filtrate was concentrated under reduced pressure and purified via column chromatography (SiO2, 1% NH4OH: 9% CH3OH: 90% CH2Cl2) to give 3.3 g of the title compound (15.6 mmol, 55% yield). MS (DCl/NH3) m/z 213 (M+H)+.

Workup

  1. filtration9% CH3OH: 90% CH2Cl2 and filtered through Celite® diatomaceous earth and silica gel
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified via column chromatography (SiO2, 1% NH4OH: 9% CH3OH: 90% CH2Cl2)

Sources & evidence

ORD record
ord-3cb2bbc6a5e94badb04556621b20db8c
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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