Catalytic hydrogenation of ethyl 2-amino-2-difluoromethyl-4-cyanobutanoate and its Schiff base reaction modes

Tetrahedron Letters

Volumn 46, Issue 16, 2005, Pages 2795-2797

  Zhu, Jingyang ^a   Price, Benjamin A ^a   Walker, Jonathan ^a   Zhao, Shannon X ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Catalyst; Catalytical hydrogenation; Eflornithin; Nitrile reduction

Indexed keywords

BUTYRIC ACID DERIVATIVE; DIAMINE; ETHYL 2 AMINO 2 DIFLUOROMETHYL 4 CYANOBUTANOATE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; HYDROGENATION; QUANTUM YIELD; REDUCTION;

EID: 15944402806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.146     Document Type: Article

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31. A typical procedure for hydrogenation: To a 460 ml hastelloy bomb is added 10% Pt-C (2.2 g) and EtOH (30 mL). The contents are agitated and pressurized under hydrogen (95 psi) for 1 h. To the vessel is then added concentrated HCl (20.8 g, 4 equiv) and 1a (20 g), as a solution in EtOH (170 mL). The contents are repressurized and agitated (500 rpm) until the starting material disappears. The reaction mix is filtered over Celite and the pad washed with 2 x 20 mL EtOH. The filtrate is then concentrated under vacuum at 40°C while EtOH (310 mL) is added to compensate for volume loss. Distillation continues until the final mass is ∼80 g. MTBE (120 mL) is then added over 10 min at 40°C to facilitate crystallization of 2. After cooling to room temperature, the slurry is agitated for 1 h, filtered over a Buchner funnel, and the cake was washed with 2 x 20 mL MTBE. After being pulled dry, the crude weight is 11.65 g (76.2% yield)