3-Cyclopentylpropionyl chloride → (R)-Methyl 3-(3-cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylate
Reaction equation
[CH3:1][NH:2][C@H:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH2:5][CH2:4]1.[CH:16]1([CH2:21][CH2:22][C:23](Cl)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[CH:16]1([CH2:21][CH2:22][C:23]([N:2]([C@H:3]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=3)[CH2:5][CH2:4]2)[CH3:1])=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(R)-Methyl 3-(methylamino)-2,3-dihydro-1H-indene-5-carboxylate (A-11) (1.61 g, 7.85 mmol, 1.0 eq.) was dissolved in DCM (50 ml); TEA (2.72 ml, 19.62 mmol, 2.5 eq.) was added at 0° C., and stirring was carried out for 15 minutes. 3-Cyclopentylpropanoic acid chloride (1.38 ml, 8.635 mmol, 1.1 eq.) was then added, and the mixture was stirred for 4 hours at RT. After monitoring by TLC, the reaction mixture was diluted with DCM (100 ml), washed with water (75 ml) and sat. NaCl solution (75 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 20% ethyl acetate in hexane). Yield: 58% (1.5 g, 4.56 mmol)
Workup
- stirringthe mixture was stirred for 4 hours at RT
- washwashed with water (75 ml) and sat. NaCl solution (75 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- custompurified by column chromatography (silica gel, 20% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-fb7400bb839a4477aba6cce9c26f98fe
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
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