Water → tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate

HRID 554468Notes

Reaction equation

HRID 554468 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:14][CH2:15][CH:16]([OH:19])[CH2:17][CH2:18]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 66701044tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

9-Oxo-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (1 g, 3.74 mmol) and cerium(III) chloride heptahydrate (1.39 g, 3.74 mmol) in methanol (40 mL) was cooled to −78° C. and sodium borohydride (141 mg, 3.74 mmol) was added in 4 portions. The mixture was warmed up to −20° C. and stirred for 30 min. Water was added and the mixture was concentrated in vacuo. The aqueous layer was extracted three times with ethyl acetate. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 883 mg (88%) of 9-hydroxy-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester as a colourless oil.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-44c2005ab26b42e5bb61a9ace6dec8c2
Source dataset
uspto-grants-2011_11
Patent number
US08049012B2

Reaction notes

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