Water → 1-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

HRID 1619370Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.B(F)(F)F.CCOCC.[N+](=[CH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N-].O>CCOCC>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3][CH:26]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (3.2 g, 16 mmol, 1.0 equiv) in Et2O (20 mL) at −50° C. were added BF3.Et2O (2.3 g, 16 mmol, 1.0 equiv) in dropwise. After completion of addition of BF3.Et2O, ethyl 2-diazoacetate (2 g, 17.6 mmol, 1.1 equiv) was added dropwise. The reaction was then stirred at −50° C. for an hour and kept at room temperature overnight. Then the reaction mixture was poured into water (100 mL), extracted with ethyl acetate (3×100 mL), combined of the organic layers and dried over Na2SO4. The solvent was removed under reduced pressure to give the desired product (4 g), which was purified by silica gel chromatography. MS (ESI): 286 (MH+).

Workup

additionwas added dropwise
extractionextracted with ethyl acetate (3×100 mL)
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-95858023187f4c5aaa3520a09cde09b1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772301B2

Reaction notes

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