5-(Benzoyl-methyl-amino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → 1h-Indole-1-carboxylic acid,5-(benzoylmethylamino)-,1,1-dimethylethyl ester

HRID 2249904Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]([C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.O=[Mn]=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]([C:19](=[O:26])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(benzoyl-methyl-amino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (500 mg) and MnO2 (5 g) in toluene (20 mL) was heated at 80° C. for 1 h. Additional MnO2 (5 g) was introduced and the resulting mixture was stirred at 80° C. for 1 h. After cooling to room temperature, the mixture was filtered through celite and the filtrate was concentrated. The product was purified by chromatography (30% EtOAc-hexanes) to give 5-(benzoyl-methyl-amino)-indole-1-carboxylic acid tert-butyl ester (372 mg, 75%).

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered through celite
concentrationthe filtrate was concentrated
customThe product was purified by chromatography (30% EtOAc-hexanes)

Sources & evidence

ORD record: ord-94ab62fecfc4451793c0c81f3a3d4319
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314936B2

Reaction notes

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