Methanol → HCID 67080673, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.90 g (8.10 mmol) of (R)-4-((S)-3-benzyloxy-1-ethoxycarbonyl-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester in 73 ml of tetrahydrofuran was treated at 0° C. with 4.44 ml (8.90 mmol, 2 M solution in tetrahydrofuran) of lithium borohydride. The reaction was stirred 10 min at 0° C. and 4 h at room temperature, again treated with 3.64 ml (7.30 mmol, 2 M solution in tetrahydrofuran) of lithium borohydride. After 16 h, 5.2 ml of methanol was added and the reaction was neutralized with cold 10% aq. potassium hydrogensulfate solution and extracted with ethyl acetate (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, 10% aq. sodium chloride solution, dried over Na2SO4 and evaporated to yield after flash silica gel column (ethyl acetate/n-heptane 1:1 to ethyl acetate, then ethyl acetate/methanol 98:2) 2.33 g (65%) of the title compound as off-white oil. MS: 441.4 (MH+).

Provenance & Evidence