(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate synthesis
- Product Name:(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate
- CAS Number:1448440-40-1
- Molecular formula:C9H10F5N3O3
- Molecular Weight:303.19
Yield:-
Reaction Conditions:
Stage #1: tert-butyl (S)-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamate;trifluoroacetic acid in acetonitrile at 0;
Stage #2: with hydrogenchloride in diethyl ether at 0; for 0.5 h;
Steps:
8
Step 8: (S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile hydrochloride. (S)-1 -(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile trifluoroacetate To a cooled (0°C) solution of (S)-iert-butyl 2-(2-cyano-4,4-difluoropyrrolidin-1 -yl)-2- oxoethylcarbamate (7.3 g, 25.2 mmol), obtained from step 7, in 1 50 ml_ of ACN was added trifluoroacetic acid (38.9 m l_, 0.505 mol) dropwise. The mixture was stirred overnight and the volatiles were evaporated. The residue was washed with ether. (S)-1 -(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile hydrochloride The residue was stirred for 30min at 0 in diethylether and dry HCI was bubbled in the reaction flask. A white solid precipitated out. The solid was collected via vacuum filtration and rinsed with cold ether and dried under vacuum to yield a whitish powder. 1 H NMR (400MHz, D20) : (5/1 mixture of trans/cis amide rotamers) 6 2.84-3.05 (m, 2H), 4.03 - 4.24 (m, 2H), 4.01 (s, 2H), 5.17 (dd, J = 8.4, 4.1 Hz, 0.8H), 5.37 (d, J = 8.4 Hz, 0.2H) Yield: 70% MS (ESI) m/z: 190.2 [M+H]+
References:
WO2013/107820,2013,A1 Location in patent:Page/Page column 47
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