Ammonium formate → 1,1-Dimethylethyl 4-[2-(3-azetidinyloxy)phenyl]-1-piperazinecarboxylate

HRID 456456Notes

Reaction equation

HRID 456456 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:24][N:23](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:22][NH:23][CH2:24]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69420117HCID 69420117, compound

Product 1

HCID 694173141,1-Dimethylethyl 4-[2-(3-azetidinyloxy)phenyl]-1-piperazinecarboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

4-[2-(1-Benzhydryl-azetidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (750 mg, 1.5 mmol) and ammonium formate (1.8 g, 30 mmol) were dissolved into methanol (50 mL) at r.t. The solution was added slowly to 10% palladium on carbon (750 mg) in methanol (20 mL) under nitrogen atmosphere. The mixture was stirred for about 48 hours and filtered through a bed of celite. The solvent was removed under reduced pressure to afford the title compound as a colorless oil (380 mg, 60%).

Workup

  1. filtrationfiltered through a bed of celite
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b2922be5e8e14ed58c3cd708e84c3137
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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