HCID 59130267, compound → HCID 59130270, compound

HRID 1992268Notes

Reaction equation

HRID 1992268 reaction equation
C1(C[N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH:12]3[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:9]2)C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH:10]12[O:15][CH:13]([CH:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:11]1)[CH2:14][NH:8][CH2:9]2

Participants

4

Reactant 1

HCID 59130267HCID 59130267, compound

Product 1

HCID 59130270HCID 59130270, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl [3-(phenylmethyl)-8-oxa-3-azabicyclo[3.2.1]oct-6-yl]carbamate (560 mg, 1.76 mmol) in EtOH (18 mL) at 25° C. was added Pd(OH)2 (336 mg, 60 wt %). The suspension was hydrogenated at 50 psi using a Parr Shaker. After 12 h, the solution was filtered through Celite®, concentrated and purified through a pad of silica (5% MeOH in DCM (1% NH4OH)) affording the title compound (400 mg, quant.) as a white solid: LC/MS (ES) m/e 229 (M+H)+.

Workup

  1. filtrationthe solution was filtered through Celite®
  2. concentrationconcentrated
  3. custompurified through a pad of silica (5% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-c8d1ec46fbcc48e58ead742727660342
Source dataset
uspto-grants-2010_01
Patent number
US07648980B2

Reaction notes

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