Diisopropylamine → 1-(4-Bromobutyl)cyclopentanecarboxylic acid methyl ester

反応式

C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]([CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>>[CH3:13][O:14][C:15]([C:17]1([CH2:26][CH2:25][CH2:24][CH2:23][Br:22])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16]

参加物

反応物 4

HCID 7912Diisopropylamine

HCID 80561,4-Dibromobutane

HCID 78365Methyl cyclopentanecarboxylate

HCID 178418339Butyllithium

生成物 1

HCID 229543431-(4-Bromobutyl)cyclopentanecarboxylic acid methyl ester

実験手順

The title compound was prepared using a similar procedure as described in Example 1, Step 1, starting from diisopropylamine (21 mL, 150 mmol), n-butyllithium (58 mL, 145 mmol), cyclopentanecarboxylic acid methyl ester (13.1 g, 100 mmol), and 1,4-dibromobutane (21.59 g, 100 mmol), and after distillation, resulted in a colorless oil (12.8 g, 48%). ES(+)-HRMS m/e calcd. for C11H19BrO2 (M+H)+ 262.0568, obsd. 262.0565.