Ethyl 5-benzyl-5-azaspiro[2.4]heptane-7-carboxylate → HCID 21978858, compound
Reaction equation
C(O[C:4]([CH:6]1[C:10]2([CH2:12][CH2:11]2)[CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5])C.[CH3:20][Li]>C(OCC)C>[CH2:13]([N:8]1[CH2:7][CH:6]([C:4](=[O:5])[CH3:20])[C:10]2([CH2:11][CH2:12]2)[CH2:9]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution (−78° C.) of 5-benzyl-5-azaspiro[2.4]heptane-7-carboxylic acid ethyl ester (Example A1a, 8.15 g, 31.4 mmol) in diethyl ether (200 mL) under a nitrogen atmosphere is treated with methyllithium (1.4 M in diethyl ether, 22.4 mL, 31.4 mmol) over a period of 10 minutes. After 1 hour, reaction mixture is warmed to −10° C. and quenched with saturated aqueous ammonium chloride. The mixture is poured into a separatory funnel and the organic layer is washed with saturated aqueous ammonium chloride, water, and brine. The organic layer is then dried with MgSO4, filtered, and the filtrate concentrated. The resulting residue is purified via flash column chromatography (1% triethylamine/7% isopropanol/92% CH2Cl2) to afford the title compound (3.93 g). MS CI: m/z 230 (MH+).
Workup
- customreaction mixture
- customquenched with saturated aqueous ammonium chloride
- additionThe mixture is poured into a separatory funnel
- washthe organic layer is washed with saturated aqueous ammonium chloride, water, and brine
- dry with materialThe organic layer is then dried with MgSO4
- filtrationfiltered
- concentrationthe filtrate concentrated
- customThe resulting residue is purified via flash column chromatography (1% triethylamine/7% isopropanol/92% CH2Cl2)
Sources & evidence
- ORD record
- ord-3cabc934875349969a6965093f8c1cd7
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582627B2
Reaction notes
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