Boron trifluoride etherate → Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

HRID 21966

Reaction equation

HRID 21966 reaction equation
C[Si]([CH2:5][C:6]1(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21])(C)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:5]=[C:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 19930812Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

Product 1

HCID 19930803Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate (0.98 g, 2.98 mmol) is dissolved in methylene chloride (50 mL), and boron trifluoride etherate (1.8 mL, 15 mmol) is added. The reaction is stirred at room temperature for 26 hours. The reaction is then quenched with saturated ammonium chloride and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (20% ethyl acetate/hexane) to give ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 91°-92° C.

Workup

  1. customThe reaction is then quenched with saturated ammonium chloride
  2. extractionextracted several times with methylene chloride
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bc023ee232b849a4ba76f663d1c2ba20
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Linked notes

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