Sodium borohydride → tert-Butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1059351Notes

Reaction equation

HRID 1059351 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12](=[O:16])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:14]([CH2:13][CH:12]([OH:16])[CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10998690tert-Butyl 5-oxohexahydrocyclopenta(c)pyrrole-2(1H)-carboxylate

Product 1

HCID 22594656tert-Butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

386 mg of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-octan-7-one synthesized in accordance with the method described in Tetrahedron, 49, 5047 (1993) was dissolved in 20 ml of ethanol. After adding 65 mg of sodium borohydride, the resulting mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After filtering, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 319 mg of the title compound as white crystals.

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
  5. filtrationAfter filtering
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f5e3d7036d3d4d3a97677fced7273e9b
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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