Triethylamine → HCID 71279909, compound

HRID 246161Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14](=O)[NH2:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>ClCCl.O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]#[N:15])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -10 °C

Procedure

In a 25 mL round bottomed flask (cis-3-carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (1.00 g, 4.13 mmol) was suspended in dichlormethane (7 mL). The suspension was cooled to −10° C. in an acetone-dry ice bath. To the cooled suspension was added slowly triethylamine (1.15 mL, 8.25 mmol) and subsequently TFAA (0.62 mL, 4.39 mmol) so that the temperature is maintained. The reaction mixture was stirred at that temperature for 3 h and then diluted with water and dichloromethane. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 60% EtOAc in heptane) to afford 0.803 g (87%) of cis-(3-cyano-cyclohexyl)-carbamic acid tert-butyl ester as a white crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ: 6.86 (d, J=7.9 Hz, 1H), 3.09-3.30 (m, 1H), 2.77 (tt, J=12.0, 3.3 Hz, 1H), 2.04 (d, J=12.1 Hz, 1H), 1.90 (d, J=9.1 Hz, 1H), 1.61-1.80 (m, 2H), 1.37 (s, 9H), 1.21-1.35 (m, 3H), 0.98-1.20 (m, 1H).

Workup

temperatureis maintained
washThe organic layer was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 0% to 60% EtOAc in heptane)

Sources & evidence

ORD record: ord-b314fd5289e549de8e86bb6ada1dc50d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

Loading…