Sodium Bicarbonate → Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

HRID 587118Notes

Reaction equation

HRID 587118 reaction equation
[O:1]=[C:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[OH:1][CH:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 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 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (600 mg, 2.5 mmol, 1.0 equiv) in MeOH (6.0 mL) was added sodium borohydride (190 mg, 5.0 mmol, 2.0 equiv) in portions at 0° C. under nitrogen. The mixture was stirred at room temperature for 2.0 hrs. The solution was concentrated by evaporator to give the white solid. Saturated NaHCO3 solution (40 mL) was added. The aqueous phase was extracted with DCM (4×30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated to give the crude which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%) to afford 334 mg (yield 57%) of tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate as a white solid.

Workup

  1. concentrationThe solution was concentrated by evaporator
  2. customto give the white solid
  3. extractionThe aqueous phase was extracted with DCM (4×30 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude which
  7. customwas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%)

Sources & evidence

ORD record
ord-f8c888775fca44afa279ba566c711b7b
Source dataset
uspto-grants-2016_01
Patent number
US09226923B2

Reaction notes

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