Benzyl chloroformate → HCID 117697513, compound

HRID 1778510Notes

Reaction equation

Cl.[CH:2]12[NH:11][CH:6]([CH2:7][C:8](=[O:10])[CH2:9]1)[CH2:5][O:4][CH2:3]2.[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>ClCCl>[O:10]=[C:8]1[CH2:9][CH:2]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH:6]([CH2:5][O:4][CH2:3]2)[CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

3-oxa-9-azabicyclo[3.3.1]nonan-7-one hydrochloride (CAS 1126795-00-3) (10 g) was dissolved in 200 ml of dichloromethane which was cooled to 0° C. Then, CbzCl (14.3 g, 84.7 mmol) was added to the mixture followed by the dropwise addition of a solution of TEA (14.6 ml, 112.8 mmol) in 20 ml of dichloromethane. The mixture was allowed to warm up to room temperature. After stirring 2 h, it was quenched with 20 ml of a saturated aqueous solution of NaHCO3. The two layers were separated and the aqueous layer was extracted with dichloromethane (3×150 ml). The combined organic layers were washed with water, dried over Na2SO4 and the solvent was evaporated under reduced pressure. The crude product was purified by chromatography on silica gel, yielding 10.1 g of benzyl 7-oxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate 100b (64%).

Workup

temperatureto warm up to room temperature
customit was quenched with 20 ml of a saturated aqueous solution of NaHCO3
customThe two layers were separated
extractionthe aqueous layer was extracted with dichloromethane (3×150 ml)
washThe combined organic layers were washed with water
dry with materialdried over Na2SO4
customthe solvent was evaporated under reduced pressure
customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-21761757798f44a291b1aaf2187accea
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266904B2

Reaction notes

Loading…