Benzyl 3,3-difluorocyclobutane-1-carboxylate → 3,3-Difluorocyclobutane-1-carboxylic acid
Reaction equation
[F:1][C:2]1([F:16])[CH2:5][CH:4]([C:6]([O:8]CC2C=CC=CC=2)=[O:7])[CH2:3]1>C(O)C.[Pd]>[F:1][C:2]1([F:16])[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of benzyl 3,3-difluorocyclobutanecarboxylate (1.4 g, 6.2 mmol) in ethanol (50 mL) was added palladium on activated carbon (500 mg) and the reaction mixture was stirred at RT under an atmosphere of hydrogen (1 atm) for 12 h. The reaction mixture was filtered through a pad of CELITE® and the filtrate was concentrated to afford Intermediate 291A as pale yellow liquid (550 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.97-12.76 (m, 1H), 3.04-2.91 (m, 1H), 2.89-2.64 (m, 4H).
Workup
- filtrationThe reaction mixture was filtered through a pad of CELITE®
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-a3d70355b97948f4a5658a443bdef9b6
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273058B2
Reaction notes
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