HCID 15058610, compound → HCID 80698473, compound

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (3.4 mL, 2M solution in THF) was added to a solution of compound 135 (114 mg, 0.69 mmol) at 0° C. and then the mixture was brought to room temperature and stirred for 4.5 h. After completion of reaction, the reaction mixture was cooled to 0° C. and carefully quenched the reaction with a saturated solution of potassium-sodium tartarate tetrahydrate by dropwise addition. The reaction mixture was filtered on a Celite bed and the filtrate was dried (Na2SO4) filtered and evaporated. The residue was purified on flash silica gel column chromatography (CH2Cl2:MeOH:NH4OH=25:1:0.1) to yield the compound 136a (which was contaminated minor amount of fluorine reduced product), yield 86 mg (74%) as a colorless syrup. 1H NMR (CD3OD, 300 MHz) δ 7.19-7.25 (m, 2H), 6.87-6.97 (m, 2H), 4.66-4.69 (m, 1H), 4.29-4.32 (m, 1H), 4.20-4.22 (m, 1H), 4.02-4.11 (m, 1H), 3.75-3.79 (m, 2H). HRMS calculated for C9H13NOF (M+H)+: 170.0981. found 170.0982. Compound 136b was prepared in a similar manner.

Provenance & Evidence