Sodium borohydride → HCID 86611601, compound

Participants

Reaction Steps

Compound 135 was prepared according to General Method 6 (EXAMPLE 3) from (7aR,10aS)-7,7a,8,9,10,10a-hexahydro-3-isopropoxy-1-(trifluoromethyl)-cyclopenta[5,6][1,4]oxazino[2,3-f]quinoline (20 mg, 0.057 mmol) and NaBH4 pellets (excess) in 7 mL TFA to afford 20 mg of (7aR,10aS)-7,7a,8,9,10,10a-hexahydro-3-isopropoxy-1-(trifluoromethyl)-7-(2,2,2-trifluoroethyl)-cyclopenta[5,6][1,4]oxazino[2,3-f]quinoline. This material (20 mg, 0.046 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 6 mL of 1:1 acetic acid:concentrated HCl (0.01 M) heated at 90° C. for 4 h to afford 15 mg (83%) of Compound 135, a yellow solid, after column chromatography (3:1 hexanes:EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3) δ12.10 (bs, 1H), 7.15 (s, 1H), 7.10 (d, J=8.8, 1H), 7.01 (d, J=8.8, 1H), 4.14 (m, 1H), 3.94 (m, 2H), 3.72 (ddd, J=10.5, 7.6, 3.4, 1H), 2.18 (m, 2H), 2.01 (m, 2H), 1.68 (m, 2H).

Provenance & Evidence