2-Cyanomethyl-5-(5'-fluoro-2-methoxyphenethyl)tetrahydrofuran → Tetrahydrofuranyl ethylamine, 14

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[C:1]([CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[O:5]1)#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[O:5]1

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To a round bottom flask under an atmosphere of Ar was added Raney Ni that was washed with methanol. Compound 12 (80 mg, 0.3 mmol), dissolved in 2 M NH3 in methanol was added to the flask. The flask was evacuated and purged with H2 once. A balloon containing H2 gas was then attached to the flask and the reaction was allowed to stir for 4 h at room temperature. The reaction mixture was filtered through a plug of Celite and the crude product obtained after the removal of the solvent was purified by preparative TLC and eluted with (MeOH/CH2Cl2, 10:90, v:v, Rf=0.1) to give the product (55 mg, 70%) as a 2:1 mixture of trans/cis diastereomers; 1H NMR: (CDCl3, 500 MHz): δ 6.87 (m, 1 H), 6.82 (dd, J=3.0, 8.5 Hz, 1 H), 6.72 (m, 1 H), 4.03 (m, 0.65 H), 3.96 (m, 0.65 H), 3.89 (m, 0.35 H), 3.82 (m, 0.35 H), 3.78 (s, 3 H), 2.68 (m, 1 H), 2.58 (m, 1 H), 2.03 (m, 2 H), 1.83 (bs, 2 H), 1.86-1.6 (m, 4 H), 1.54 (m, 2 H); HRMS (ESI) [M+H]+ calcd for C15H23FNO2 268.1713, found 268.1701; HPLC>96% pure (tR=4.66 min, 40(A):55(B):5(C):0.01(D); tR=5.05 min, 10(A):85(B):5(C):0.01(D)).