Phenylmethyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-8-azaspiro[4.5]decane-8-carboxylate → 1,1-Dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamate

HRID 734228Notes

Reaction equation

HRID 734228 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH:13]([OH:14])[CH2:12][C:11]2([CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][CH2:15]2)[CH2:10]1)=[O:7])([CH3:4])[CH3:3]>CCO.[OH-].[OH-].[Pd+2]>[OH:14][CH:13]1[CH2:12][C:11]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:10][CH:9]1[NH:8][C:6](=[O:7])[O:5][C:2]([CH3:3])([CH3:1])[CH3:4]

Participants

4

Reactant 1

HCID 69054060Phenylmethyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 765808691,1-Dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamateYield 31%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of phenylmethyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (˜3.1 g, 7.65 mmol) in EtOH (38 mL) was added Pd(OH)2 (1.5 g, 50 wt %). The solution was hydrogenated using a Parr Shaker at 50 psi. After 2 h, the solution was filtered through Celite®, concentrated and purified by column chromatography (silica, 15% MeOH in DCM (1% NH4OH)) yielding the title compound (618 mg, 31%-2 steps) as a yellow oil: LCMS (ES) m/e 272 (M+H)+.

Workup

  1. filtrationthe solution was filtered through Celite®
  2. concentrationconcentrated
  3. custompurified by column chromatography (silica, 15% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-08d2255fd3c7486f82e7d40cbf642e9e
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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