Methanol → HCID 86705493, compound

Participants

Reaction Steps

To a solution of 166 (10.85 g, 21.09 mmol), DCM (100 mL) and MeOH (10 mL) was added HCl/dioxane (26.36 mL, 105.4 mmol, 4N solution in dioxane) and the reaction was stirred for 18 h. The solution was concentrated to afford a red oil. To the residue was added DCM/methanolic NH3 (100 mL, 9:1, 7N) and the mixture sonicated for 5 min. The filtrate was concentrated to afford a thick red oil. The crude product was purified by SiO2 chromatography (Biotage 40 M) eluting with DCM/7N methanolic:NH3 (4:1 then 9:1 solution) to afford 4.1 g (80%) of (1S,3S)-3-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)cyclopentanol (168) as a light brown oil: MS m/z (APCI-pos) M+1=235.2.

Provenance & Evidence