Sodium borohydride → HCID 86659850, compound

HRID 2402758Notes

Reaction equation

HRID 2402758 reaction equation
[N:1]1([CH:6]2[CH2:20][C@@H:9]3[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C@@H:8]3[C:7]2=[O:21])[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+]>CO>[OH:21][CH:7]1[C@@H:8]2[C@@H:9]([CH2:10][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:12]2)[CH2:20][CH:6]1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86659848HCID 86659848, compound

Product 1

HCID 86659850HCID 86659850, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3aR,6aS)-tert-Butyl 5-(1H-imidazol-1-yl)-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (75 mg, 0.257 mmol) from Step 2 in methanol (2 mL) was cooled in a dry ice/acetone bath to −78° C., and sodium borohydride (11.69 mg, 0.309 mmol) was added. The reaction was allowed to warm to ambient temperature over 6 hours. Then the reaction mixture was partially concentrated, quenched with 10 mL of aqueous ammonium chloride, diluted with water, and extracted with 2×20 mL of ethyl acetate. The extracts were washed with brine, dried (Na2SO4) and filtered. The solvent was removed in vacuo. The crude product was purified using a 4 g silica gel cartridge with a gradient of 0-6% CH3OH (2 N NH3)/CH2Cl2 over 20 minutes to give (3aR,6aS)-tert-butyl 4-hydroxy-5-(1H-imidazol-1-yl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate.

Workup

  1. concentrationThen the reaction mixture was partially concentrated
  2. customquenched with 10 mL of aqueous ammonium chloride
  3. additiondiluted with water
  4. extractionextracted with 2×20 mL of ethyl acetate
  5. washThe extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customThe crude product was purified
  10. customover 20 minutes

Sources & evidence

ORD record
ord-360f68bdf83343c3a0f1df0220f52ebb
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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