Diisopropylamine → HCID 58171524, compound
Reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH2:13]([O:15][C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][CH:27]2[CH:34]3[CH2:35][CH:30]4[CH2:31][CH:32]([CH2:36][CH:28]2[CH2:29]4)[CH2:33]3)=[O:25])[CH2:19]1)=[O:17])[CH3:14].[CH3:37][O:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41]Br>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1([CH2:41][C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[O:38][CH3:37])[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][CH:27]2[CH:28]3[CH2:29][CH:30]4[CH2:31][CH:32]([CH2:33][CH:34]2[CH2:35]4)[CH2:36]3)=[O:25])[CH2:19]1)=[O:17])[CH3:14]Participants
6
Conditions
- Temperature
- -70 °C
Procedure
To a stirred solution of diisopropylamine (6.3 g, 62.7 mmol) in dry THF (120 mL) at −20° C. under N2 was added 2.5 M n-BuLi (25.1 mL, 62.7 mmol). The resulting solution was added dropwise to a stirred solution of 1-(2-adamantyl) 3-ethoxycarbonylpiperidine-1-carboxylate (14.0 g, 41.8 mmol) in dry THF (170 mL) at −70° C. The mixture was stirred for 1 h at −70° C. and 2-methoxybenzyl bromide (10.9 g, 54.3 mmol) was added. The mixture was stirred for 4 h at rt, quenched with brine and extracted with CH2Cl2. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography to afford the title compound (14.3 g, 75%). LC-MS Method 3 tR=2.04 min, m/z=456.
Workup
- stirringThe mixture was stirred for 4 h at rt
- customquenched with brine
- extractionextracted with CH2Cl2
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-e97c2dc385ed4032bd8c979eec6f8041
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163012B2
Reaction notes
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