Diisopropylethylamine → Methyl 4-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2,3-dihydro-1H-indene-2-carboxylate

HRID 877181Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]2.C(N(CC)C(C)C)(C)C.[Br:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[C:33](Cl)=[O:34])=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[C:33]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH:5]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]3)=[O:34])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

235 mg (1.228 mmol) of methyl 4-amino-2,3-dihydro-1H-indene-2-carboxylate (racemic; Example 88A) were dissolved in 10 ml of THF, and 428 mg (4.911 mmol) of N,N-diisopropylethylamine and 388 mg (1.228 mmol) of [4-(bromomethyl)phenyl](cyclopentyl)acetyl chloride were added at 0° C. The mixture was stirred at 0° C. for 30 min. Saturated aqueous sodium bicarbonate solution was then added, and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. This gave 577 mg of the title compound.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-499424dea51143b69714a7ff30b7fda4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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