2-Methylbenzoyl chloride → (R)-Methyl 3-(2-methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1253643Notes

Reaction equation

HRID 1253643 reaction equation
C(N(C(C)C)C(C)C)C.[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].Cl.[CH3:21][O:22][C:23]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH2:30][CH2:29][C@H:28]2[NH2:34])=[O:24]>C(Cl)Cl.C(OCC)(=O)C>[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:34][C@H:28]1[C:27]2[C:31](=[CH:32][CH:33]=[C:25]([C:23]([O:22][CH3:21])=[O:24])[CH:26]=2)[CH2:30][CH2:29]1)=[O:14]

Participants

6

Reactant 3

HCID 702762-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 66700566(R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride

Product 1

HCID 59505253(R)-Methyl 3-(2-methylbenzamido)-2,3-dihydro-1H-indene-5-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Ethyl-diisopropylamine (2.5 eq.) and 2-methylbenzoyl chloride (1.2 equiv.) were added to an ice-cold solution of (3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-03 HCl) (0.88 mmol, 1 equiv.) in methylene chloride at 0° C. under an inert atmosphere and the mixture was then stirred at room temperature for 2 d. The reaction mixture was diluted with ethyl acetate and the organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution. The organic phase was dried over Na2SO4 and concentrated to obtain the crude product, which was purified by column chromatography (silica, cyclohexane/ethyl acetate 4:1). Yield: 70%

Workup

  1. washthe organic phase was washed with 10% NH4Cl solution, sat. NaHCO3 solution and sat. NaCl solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e171a51ed4ff42a6baef437aebef62a4
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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