1463522-73-7 → Cyclobutaneacetic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl ester

HRID 1855605Notes

Reaction equation

HRID 1855605 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][C:11](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 867010551463522-73-7

Product 1

HCID 86701059Cyclobutaneacetic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl esterYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (360 mg) was added to a solution of ethyl 2-(3-(tert-butoxycarbonylamino)cyclobutylidene)acetate (1.2 g, 4.8 mmol) in MeOH (10 mL) at 23° C. The reaction mixture was stirred under a H2 balloon at rt for 1.5 hrs. The mixture was filtered and concentrated. The residue was purified by silica gel column (10% EtOAc/petroleum ether) to afford ethyl 2-(3-(tert-butoxycarbonylamino)cyclobutyl)-acetate (1.2 g, 96%). ESI-MS (EI+, m/z): 258 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column (10% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-26bb08edcba34753bcec55c0d88d1269
Source dataset
uspto-grants-2015_02
Patent number
US08962844B2

Reaction notes

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