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

HRID 877181ノート

反応式

HRID 877181 の反応式
[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

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 53350286Methyl 4-amino-2,3-dihydro-1H-indene-2-carboxylateHCID 58136560[4-(Bromomethyl)phenyl](cyclopentyl)acetyl chloride

生成物 1

HCID 58136756Methyl 4-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2,3-dihydro-1H-indene-2-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-499424dea51143b69714a7ff30b7fda4
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

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