Ammonium Chloride → Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

HRID 2300177Notes

Reaction equation

HRID 2300177 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:5]1.[Cl-].[NH4+]>C(O)C>[OH:3][CH:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:5]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 9834677Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

300 ml ethanol was ice-cooled, and 6.13 g of sodium borohydride was dissolved therein. 100 ml solution of 38.9 g of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate in ethanol was added dropwise thereinto over 25 min. The reaction solution was treated with saturated aqueous ammonium chloride and evaporated. The resulting residue was partitioned into ethyl acetate and water, and the ethyl acetate layer was washed with brine and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 36.6 g of tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe resulting residue was partitioned into ethyl acetate and water
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-be099c1494bf48e08535a3c567748fca
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

Loading…