Acetic Acid → HCID 117601123, Verbindung

Temperatur

20 °C

Combined tert-butyl 6,6-difluoro-1,4-diazepane-1-carboxylate (49 mg, 0.207 mmol) and sodium cyanoborohydride (52 mg, 0.83 mmol) in THF (1.5 mL) and added 37% aqueous formaldehyde (0.077 mL, 1.037 mmol) and acetic acid (0.018 mL, 0.311 mmol) and then stirred at 20° C. for 16 h. Then methanol (300 uL) was added and the mixture was concentrated in vacuo to give a residue which was taken up in ethyl acetate (40 mL), washed with saturated aqueous sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate and concentrated in vacuo to give the title compound (51 mg, 0.204 mmol, 98%) as a clear, colorless oil. MS: 251 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H) 2.50 (s, 3 H) 2.73 (d, J=4.8 Hz, 2 H) 2.92 (t, J=13.5 Hz, 2 H) 3.55 (d, J=4.8 Hz, 2 H) 3.75-3.94 (m, 2 H).

1. concentrationthe mixture was concentrated in vacuo
2. customto give a residue which
3. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine
4. dry with materialdried with magnesium sulfate
5. concentrationconcentrated in vacuo

ORD-Eintrag

ord-21de13718b3c4e13a831828d94616203

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09040522B2