Hydrochloric Acid → HCID 86616401, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of oxalyl chloride (0.91 mL, 10.4 mmol) in CH2Cl2 (40 mL) at −78° C. was added DMSO (1.48 mL, 20.9 mmol), dropwise, over 5 min. The reaction mixture was stirred for 30 min, during which time it warmed to −60° C., then a solution of tert-butyl [4,6-difluoro-1-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl]carbamate from Step E (2.08 g, 6.95 mmol) in CH2Cl2 (22 mL) was added, dropwise, over 30 min. During the addition, the reaction temperature rose to −45° C. and it was stirred at this temperature for an additional 15 min. To the resulting mixture was added N,N-diisopropylethylamine (7.28 mL, 41.7 mmol), dropwise, over 2 min. The mixture was allowed to warm to 0° C., stirred for 15 min then poured into ice (60 mL) and 1 N aqueous HCl (30 mL). The resulting mixture was extracted with CH2Cl2 (2×100 mL). The combined organic extracts were washed with H2O (30 mL), then brine (50 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=224 (M−OC4H9).

Provenance & Evidence