HCID 53410921, compound → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 582529Notes

Reaction equation

HRID 582529 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][CH:11](NCC2C=CC=CC=2)[CH:10]([OH:21])[CH2:9]1)=[O:7])([CH3:4])[CH3:3]>C(O)C.C(OCC)(=O)C.[Pd]>[CH3:4][C:2]([CH3:1])([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:11]([O:21]2)[CH2:12]1)=[O:7])[CH3:3]

Participants

5

Reactant 1

HCID 53410921HCID 53410921, compound

Product 1

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateYield 92.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [trans-(+/-)]-3-hydroxy-4-[(phenylmethyl)amino]-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (1.1 g, 3.76 mmol) in ethanol (150 ml) was hydrogenated over 10% palladium-on-carbon (0.05 g) for 3.5h. The catalyst was removed by filtration, washed with ethanol (50 ml) and the combined ethanolic solution was evaporated to leave an oil which was taken up in ethyl acetate (75 ml). The solution was filtered and the filtrate evaporated to leave a solid which was crystallised from ethyl acetate/cyclohexane to give the title compound (0.643 g), nmr(δ,CDCl3) 1.45(s, 9H), 1.6-2.2(bm, 3H), 3.1(m,1H), 3.3(m,2H), 3.68(m,2H), 3.98(m,1H).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol (50 ml)
  3. customthe combined ethanolic solution was evaporated
  4. customto leave an oil which
  5. filtrationThe solution was filtered
  6. customthe filtrate evaporated
  7. customto leave a solid which
  8. customwas crystallised from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-34669698ef2c4b9480e707e8530ec32c
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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