HCID 59361395, compound → HCID 67302960, compound

HRID 888893Notes

Reaction equation

HRID 888893 reaction equation
C([O:8][CH2:9][C:10]([N:12]1[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[N:13]1[CH:19]1[CH:26]2[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:28][CH:20]1[CH2:21]3)[CH2:25]2)=[O:11])C1C=CC=CC=1>C(O)C.[C].[Pd]>[CH3:16][C:15]1([CH3:17])[N:12]([C:10](=[O:11])[CH2:9][OH:8])[N:13]([CH:19]2[CH:20]3[CH2:21][CH:22]4[CH2:23][CH:24]([CH2:25][CH:26]2[CH2:27]4)[CH2:28]3)[C:14]1=[O:18]

Participants

4

Reactant 1

HCID 59361395HCID 59361395, compound

Product 1

HCID 67302960HCID 67302960, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-[(benzyloxy)acetyl]-4,4-dimethyl-2-(adamantan-2-yl)-1,2-diazetidin-3-one (151 mg, 0.400 mmol) prepared in Example 263 in ethanol (3 mL) was added with 10% palladium carbon (catalyst amount), and under a hydrogen atmosphere the resultant was stirred at room temperature for 20 hours. The reaction solution was filtered using celite, concentrated in vacuo, the obtained residue was purified using silica gel chromatography (hexane:ethyl acetate=2:1), and 4,4-dimethyl-1-(hydroxyacetyl)-2-(adamantan-2-yl)-1,2-diazetidin-3-one (52.0 mg, 44.5%) was obtained as a white crystalline powder.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated in vacuo
  3. customthe obtained residue was purified

Sources & evidence

ORD record
ord-c7584a2a4c464926972532bc37bc0913
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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