HCID 67303368, compound → HCID 67303639, compound

HRID 888766Notes

Reaction equation

HRID 888766 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:14](=[O:15])[CH2:13][N:12]1C(OCC1C=CC=CC=1)=O)[CH2:8]2>O1CCCC1.[C].[Pd]>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[C:14](=[O:15])[CH2:13][NH:12]1)[CH2:10]2

Participants

4

Reactant 1

HCID 67303368HCID 67303368, compound

Product 1

HCID 67303639HCID 67303639, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 2-(adamantan-2-yl)-3-oxo-1,2-diazetidine-1-carboxylate (100 mg, 0.29 mmol) in tetrahydrofuran (5 mL) was added with 10% palladium carbon (catalyst amount), and under a hydrogen atmosphere, the resultant was stirred at room temperature for 10 hours. The reaction solution was filtered using celite, concentrated in vacuo, and the obtained residue was purified using silica gel chromatography (hexane:ethyl acetate=1:1), and 2-(adamantan-2-yl)-1,2-diazetidin-3-one (34.0 mg, 56.8%) was obtained as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-d858d42aa9594c8d9202fbfea3367192
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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