Reaction #42219

Reaction equation

Intermediate 7

methyl 4-methylbenzenesulfonate

(±)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methanamine

diisopropylethylamine

benzyl chloroformate

→

(±)-benzyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate

Yield 89.0%

Conditions

Procedure

Treatment of (±)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methanamine (0.83 g, 3.07 mmol) with diisopropylethylamine (1.20 g, 9.28 mmol) followed by benzyl chloroformate (0.79 g, 4.60 mmol) generally according to the procedure described for Intermediate 7 provided 1.00 g (89%) of (±)-benzyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate as a white solid. mp 117-119° C.; Anal. calcd. for C21H18ClNO3.0.5H2O: C, 66.93; H, 5.08; N, 3.72. Found: C, 66.81; H, 4.96; N, 3.67.

Source