HCID 59361467, compound → HCID 59361525, compound

HRID 888857Notes

Reaction equation

HRID 888857 reaction equation
[CH3:1][C:2]1([CH3:28])[N:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[O:7])[N:4]([CH:17]2[CH:24]3[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:26][CH:18]2[CH2:19]4)[CH2:23]3)[C:3]1=[O:27]>C(O)C.O1CCCC1.[C].[Pd]>[NH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]([N:5]1[C:2]([CH3:1])([CH3:28])[C:3](=[O:27])[N:4]1[CH:17]1[CH:24]2[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:26][CH:18]1[CH2:19]3)[CH2:23]2)=[O:7]

Participants

4

Reactant 1

HCID 59361467HCID 59361467, compound

Product 1

HCID 59361525HCID 59361525, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4,4-dimethyl-1-[(2-nitrophenyl)carbonyl]-2-(adamantan-2-yl)-1,2-diazetidin-3-one (16.7 mg, 0.0436 mmol) prepared in Example 124 in ethanol-tetrahydrofuran was added with 10% palladium carbon (catalyst amount), and under a hydrogen atmosphere, the resultant was stirred at room temperature for 1 hour. The reaction solution was filtered using celite and concentrated in vacuo. The obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=2:1), and the title compound (14.8 mg, 96.1%) was obtained as a white crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-cd343968be74484db92e5959c6ecf3c5
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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