HCID 70873766, compound → HCID 86719579, compound

HRID 2208947Notes

Reaction equation

HRID 2208947 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([N+:24]([O-])=O)[C:22]=1[CH3:23])[O:8][CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1)=[O:4]>CO.[Pd]>[NH2:24][C:21]1[CH:20]=[C:7]([CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:22]=1[CH3:23])[O:8][CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1

Participants

4

Reactant 1

HCID 70873766HCID 70873766, compound

Product 1

HCID 86719579HCID 86719579, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To stirred solution of tert-butyl 3-(3-(methoxycarbonyl)-4-methyl-5-nitrophenoxy)azetidine-1-carboxylate (1.0 g, 2.7 mmol) in methanol (10 mL) was added a catalytic amount of 10% Pd/C. The mixture was stirred at room temperature under a hydrogen atmosphere (balloon pressure) for 3 hours. On completion, the reaction mixture was filtered through a celite bed which was further washed with methanol. The combined filtrates were concentrated under reduced pressure to afford the title compound (0.90 g, 98%).

Workup

  1. filtrationOn completion, the reaction mixture was filtered through a celite bed which
  2. washwas further washed with methanol
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-78e4b500eba54af79003987105960767
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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