Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate → Ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate

HRID 1523724Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=O)[CH:12]2[CH:10]([CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 3-benzyl-2,4-dioxo-3-aza bicyclo[3.1.0]hexane-6-carboxylate (SYNLETT, 1996, 1097; 5.0 grams, 18.3 mmol) in tetrahydrofuran (74 mL) cooled at 0° C., BH3-DMS (2N solution in tetrahydrofuran 36 mL, 73.2 mmol) was added over a period of 30 minutes. The reaction temperature was gradually raised to reflux for 6 hours. After cooling the reaction mixture to 0° C., it was quenched by adding aqueous ammonium chloride solution and was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain ethyl 3-benzyl-3-aza bicyclo[3.1.0]hexane-6-carboxylate (2.8 grams)

Workup

temperatureThe reaction temperature was gradually raised
temperatureto reflux for 6 hours
customit was quenched
additionby adding aqueous ammonium chloride solution
extractionwas extracted with ethyl acetate
dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
customthe solvent was removed under reduced pressure
customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-240e4f757abf4ee3af472c74400d59d9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079894B2

Reaction notes

Loading…