Formaldehyde → 10-Chloro-1,2-dimethyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

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Reaction Steps

10-Chloro-1-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole trifluoroacetate (Example 98, 59 mg, 0.15 mmol) in MeOH (1 mL) was converted to the free amine by PL-HCO3 MP SPE (Polymer Laboratories) column. Formaldehyde (37 wt. % in H2O, 0.20 mL, 2.4 mmol) was added to a solution of the free amine (0.15 mmol) in THF (1 mL). After stirring for 10 minutes at room temperature sodium triacetoxyborohydride (26 mg, 0.12 mmol) was added and the mixture was stirred for an additional 30 minutes and evaporated. The crude material was purified by preparative HPLC (Xterra C18, 10 mM NH4HCO3 (pH 10) —CH3CN) to give the title compound as a white solid (28.9 mg). MS m/z 391 [M+H]+.

Provenance & Evidence