HCID 71240325, compound → tert-Butyl 7-hydroxy-2-azaspiro[3.5]nonane-2-carboxylate

HRID 587127Notes

Reaction equation

HRID 587127 reaction equation
C([O:8][CH:9]1[CH2:24][CH2:23][C:12]2([CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[OH:8][CH:9]1[CH2:10][CH2:11][C:12]2([CH2:15][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:13]2)[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 71240325HCID 71240325, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71239877tert-Butyl 7-hydroxy-2-azaspiro[3.5]nonane-2-carboxylateYield 94.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 7-(benzyloxy)-2-azaspiro[3.5]nonane-2-carboxylate (290 mg, 0.96 mmol, 1.0 equiv) in MeOH (8 mL) was added Pd(OH)2 (43.5 mg, 15 wt %). The mixture was carefully vacuumed and refilled with Hydrogen. The mixture was then stirred at room temperature under hydrogen balloon for 2 hrs. The mixture was passed through a pad of celite and eluted with MeOH (50 mL). The combined methanol solution was concentrated to afford 218 mg (yield 94%) of tert-butyl 7-hydroxy-2-azaspiro[3.5]nonane-2-carboxylate as a pale yellow solid.

Workup

  1. washeluted with MeOH (50 mL)
  2. concentrationThe combined methanol solution was concentrated

Sources & evidence

ORD record
ord-7b708b7f292b481e8d715fe49c3a8d70
Source dataset
uspto-grants-2016_01
Patent number
US09226923B2

Reaction notes

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