Diglyme → HCID 22822244, compound

Participants

Reaction Conditions

Reaction Steps

Lithium chloride (1.01 g), sodium borohydride (0.91 g) and diglyme (diethylene glycol dimethyl ether) (100 cc) are mixed at 0° C. The mixture is stirred for 30 minutes at 0° C. and (S)-3-[(3-methoxycarbonylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (4.7 g) is added. Stirring is continued for 1 hour at 0° C. and then for 2 hours at 20° C. Water (1 liter) is added and the mixture is extracted with methylene chloride (3×150 cc). The organic extracts are combined, washed with water, dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (40 mm Hg; 5.3 kPa) at 40° C. The residue is dissolved in methylene chloride (20 cc) and the solution is poured onto a column of diameter 3 cm, containing silica gel (120 g) in methylene chloride. Elution is carried out with an ethyl acetate/cyclohexane mixture (70/30 by volume), 300 cc fractions being collected. Fractions 7 to 11 are combined and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue is recrystallised from butyl acetate (100 cc). After filtration, washing with diisopropyl ether and drying, (S)-3-[(3-hydroxymethylisoquinol-5-yl)-imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (2 g) is obtained, as a white solid, m.p.=210° C.

Provenance & Evidence