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

Temperature

22 °C

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).

1. washwashed with sat. NaHCO3 (50 ml)
2. extractionThe sat NaHCO3 was back extracted with CH2Cl2
3. washthe combined organic layers were washed with brine (50 ml)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customproviding an oily residue, which
7. temperaturerefluxed for 1 hour
8. customThe MeOH was evaporated
9. customthe crude was triturated with ether
10. filtrationfiltered

ORD record

ord-4f07f5380cd64e0193ee96c8ce747497

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718647B2