Triethylamine → (Rac)-2-(2-chloro-benzyl)-7a-methyl-hexahydro-pyrrolo[1,2-c]imidazol-3-one
Reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1([CH3:12])[CH2:11][CH2:10][CH2:9][NH:8]1.Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:6][C:7]2([CH3:12])[CH2:11][CH2:10][CH2:9][N:8]2[C:18]1=[O:20]Participants
Procedure
To a cold (0° C.) solution of (2-chloro-benzyl)-((rac)-2-methyl-pyrrolidin-2-ylmethyl)-amine (0.5 g, 1 eq) in DCM (15 mL) was added a solution of triphosgene (0.5 eqv) in DCM (5 mL) over a period of 5 minutes followed by the addition of triethylamine (3 eq). The reaction mixture was allowed to stir for 4 h. After the completion of the reaction on TLC, the reaction mixture was quenched with 1M HCl (10 mL) and extracted with DCM (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated using rotary evaporator to give sticky crude, which was then purified with column chromatography (1-2% Methanol:DCM, Mesh Size-100-200 silica, Diameter of column—2.5 cm, Height of silica—approx. 5 inch) to afford the desired product (rac)-2-(2-chloro-benzyl)-7a-methyl-hexahydro-pyrrolo[1,2-c]imidazol-3-one as white solid (22-70%). MS (ES+): 265.5 (MH+))
Workup
- customAfter the completion of the reaction on TLC
- customthe reaction mixture was quenched with 1M HCl (10 mL)
- extractionextracted with DCM (3×50 mL)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customevaporator
- customto give sticky crude, which
- customwas then purified with column chromatography (1-2% Methanol:DCM, Mesh Size-100-200 silica, Diameter of column—2.5 cm, Height of silica—approx. 5 inch)
Sources & evidence
- ORD record
- ord-19d4e51a0d704a979eb5888420ea8815
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124636B2
Reaction notes
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