Sodium borohydride → HCID 71060241, compound

HRID 1036717Notes

Reaction equation

HRID 1036717 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][CH2:22][C:10]2([N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:13]=[N:12][C:11]2=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][CH2:22][C:10]2([N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][NH:12][C:11]2=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71060280HCID 71060280, compound

Product 1

HCID 71060241HCID 71060241, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-oxo-1-phenyl-1,3,7-triaza-spiro[4.5]dec-2-ene-7-carboxylic acid tert-butyl ester (130 mg, 0.39 mmol) in methanol (3 ml) was added sodium borohydride (22 mg, 0.59 mmol). The reaction mixture was stirred at RT for 1 hour. The reaction mixture was concentrated in vacuo. The residue was dissolved with EtOAc (5 ml) and washed with a saturated solution of sodium bicarbonate (10 ml). The aqueous phase was extracted with further EtOAc (5 ml). The organics portions were combined, dried (MgSO4) and concentrated in vacuo to afford an oil. Purification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved with EtOAc (5 ml)
  3. washwashed with a saturated solution of sodium bicarbonate (10 ml)
  4. extractionThe aqueous phase was extracted with further EtOAc (5 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto afford an oil
  8. customPurification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-0bce9d4611a24f6a85146c05a605dacb
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

Loading…