1-Chloroethyl chloroformate → 5,6,7,8-Tetrahydro-4H-furo[2,3-d]azepine Hydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of the product from step f) (2.56 mg, 11.3 mmol) in anhydrous dichloroethane (56 ml) was cooled to 0° C., treated with 1-chloroethyl chloroformate (6.11 ml, 56.4 mmol) and the reaction was warmed to 22° C. for 1 hour. The reaction was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3 (50 ml). The sat NaHCO3 was back extracted with CH2Cl2 and the combined organic layers were washed with brine (50 ml), dried (MgSO4) and concentrated providing an oily residue, which was taken up in anhydrous MeOH (150 ml) and refluxed for 1 hour. The MeOH was evaporated and the crude was triturated with ether and filtered providing 1.71 g (87%) of the subtitle compound. 1H NMR (300 MHz, DMSO) δ 9.56 (br s, 2H); 7.43 (d, J=2 Hz, 1H); 6.34 (d, J=2 Hz, 1H); 3.18-3.30 (br m, 4H); 3.03-3.10 (br m, 2H); 2.74-2.82 (br m, 2H); MS: ESI (positive): 138 (M+H).

Provenance & Evidence