5-(p-Fluorophenyl)-2-hydroxytetrahydrofuran → Flutroline

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]3[CH2:18][CH2:19][N:20]([C:22](OCC4C=CC=CC=4)=O)[CH2:21][C:5]=3[C:4]=2[CH:3]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[O:43]C(O)[CH2:41][CH2:40]2)=[CH:35][CH:34]=1>C(OCC)(=O)C.[Pd]>[F:17][C:14]1[CH:15]=[CH:16][C:11]2[N:7]([C:8]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[C:6]3[CH2:5][CH2:21][N:20]([CH2:22][CH2:41][CH2:40][CH:39]([C:36]4[CH:35]=[CH:34][C:33]([F:32])=[CH:38][CH:37]=4)[OH:43])[CH2:19][C:18]=3[C:12]=2[CH:13]=1

Participants

Procedure

In a Parr bottle were combined 5% Pd/C (5 g of 50% water-wet), 8-fluoro-5-(p-fluorophenyl)-2-carbobenzoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (5.0 g, 0.0119 mole) in 100 ml ethyl acetate, and 5.5 grams (0.03 mole) 5-(p-fluorophenyl)-2-hydroxytetrahydrofuran in 100 ml ethyl acetate. The mixture was agitated and hydrogenated at 30-40 psig for 20 hours. The solution was filtered to recover catalyst, with ethyl acetate and CH2Cl2 wash. The filtrate and washes were concentrated in vacuo to a viscous oil. The oil was dissolved in 400 ml ethyl acetate and filtered. The solution was concentrated to an oil, diluted with 150 ml ether, and filtered to yield title product, 3.8 gm, m.p. 145°-149° C.