Methanol → HCID 68832620, compound

HRID 2109863Notes

Reaction equation

HRID 2109863 reaction equation
[C:1]([N:4]1[CH:10]2[CH:8]([CH:9]2[C:11](OCC)=[O:12])[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:6](=[O:24])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].CO>CCO>[C:1]([N:4]1[CH:10]2[CH:8]([CH:9]2[CH2:11][OH:12])[N:7]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[C:6](=[O:24])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 57634640HCID 57634640, compound

Product 1

HCID 68832620HCID 68832620, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the exo isomer of ethyl 5-acetyl-2-(4-fluorobenzyl)-3-oxo-2,5-diazabicyclo[4.1.0]heptane-7-carboxylate (3.3 g, 9.87 mmol) in 32 ml EtOH at room temperature was added sodium borohydride (398 mg, 10.5 mmol). After stirring overnight, the reaction mixture was treated with 200 mL MeOH, stirred for 1 h and then concentrated. The residue was dissolved in dichloromethane (100 mL), treated with 1N HCl (10 mL) and water (20 mL). The aqueous phase was back extracted with chloroform (2×50 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel using ethyl acetate and methanol as eluents to give title product.

Workup

  1. stirringstirred for 1 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  4. additiontreated with 1N HCl (10 mL) and water (20 mL)
  5. extractionThe aqueous phase was back extracted with chloroform (2×50 mL)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-73d8250ba54e442aba29a402153d4d67
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

Loading…