Dimethyl Sulfide → HCID 118223831, Verbindung

A solution of benzyl 6-amino-5-oxo-1,4-diazepane-1-carboxylate (12.86 g, 47.4 mmol) in THF (158 mL) was treated dropwise with BH3.DMS (22.5 mL, 237 mmol). The mixture was warmed to reflux and stirred for 15 hours. The mixture was then cooled to 0 OC, quenched by the slow addition of MeOH (50 mL; vigorous H2 evolution observed) and treated over 10 min with concentrated HCl (12 mL). The reaction vessel was then heated to reflux for 8 hours. The volatiles were partially removed under reduced pressure and the mixture was basified to pH 11 with solid Na2CO3. The aqueous layer was extracted with CH2Cl2 (2×), the organic phase was dried (Na2SO4), and concentrated in vacuo to afford benzyl 6-amino-1,4-diazepane-1-carboxylate (I-54a). MS calculated for C13H20N3O2 (M+H+) 250.15. found 250.1. The crude was used in the next step without further purification.

1. temperatureThe mixture was warmed
2. temperatureto reflux
3. temperatureThe mixture was then cooled to 0 OC
4. customquenched by the slow addition of MeOH (50 mL; vigorous H2 evolution observed)
5. additiontreated over 10 min with concentrated HCl (12 mL)
6. temperatureThe reaction vessel was then heated
7. temperatureto reflux for 8 hours
8. customThe volatiles were partially removed under reduced pressure
9. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
10. dry with materialthe organic phase was dried (Na2SO4)
11. concentrationconcentrated in vacuo

ORD-Eintrag

ord-5accb799def34b3295ee8f4e1890eae3

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440957B2