Methyl chloroformate → HCID 66915470, compound
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].Cl[C:34]([O:36][CH3:37])=[O:35]>O1CCCC1>[CH3:37][O:36][C:34]([C:10]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:24])=[O:35]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
A solution of 1 mmol of 1-benzyl-3-(2,4-dimethoxy-phenyl)-piperidin-2-one [597553-90-7] in 20 ml of tetrahydrofuran is cooled to −70° C. and treated drop wise with a solution of 1.2 mmol of lithium diisopropyl-amide in 5 ml of tetrahydrofuran. The mixture is stirred 15 minutes at −70° C. A solution of 1.2 mmol of methyl chloroformate in 5 ml of tetrahydrofuran is added at −70° C. and the reaction mixture is allowed to come to room temperature over a period of 7 hours. The reaction mixture is quenched with water and extracted with tert-butyl methyl ether (3×). The combined organic phases are dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.
Workup
- waitto come to room temperature over a period of 7 hours
- customThe reaction mixture is quenched with water
- extractionextracted with tert-butyl methyl ether (3×)
- dry with materialThe combined organic phases are dried with sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-1143ed24f2e04ebeac7a9b6b3764332e
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071774B2
Reaction notes
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