Diisopropylethylamine → Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

HRID 16589

反応式

I[CH2:2][C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:12]([O:16][C:17](=[O:26])[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>CN1CCCC1=O.C([O-])(O)=O.[Na+]>[C:12]([O:16][C:17]([NH:18][CH2:19][CH:20]1[CH2:21][CH2:22][N:23]([CH2:2][C:3]2([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:24][CH2:25]1)=[O:26])([CH3:15])([CH3:13])[CH3:14]

参加物

反応条件

温度: 120 °C

実験手順

A mixture of Methyl 1-(iodomethyl)cyclopentanecarboxylate(5.52 g, 0.0206 mol, Step 1), tert-butyl(piperidin-4-ylmethyl)carbamate (8.83 g, 0.0412 mol) and iPr2NEt (10.76 mL, 0.0618 mol) in N-methylpyrrolidone (70 mL) was stirred at 120° C. for 24 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (200 mL), extracted with AcOEt (200 mL) for three times, and the combined organic layer was washed with water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1) to give 4.91 g (67%) of title compound as a yellow syrup.

後処理

temperatureAfter cooling
extractionextracted with AcOEt (200 mL) for three times
washthe combined organic layer was washed with water (200 mL) and brine (200 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customRemoval of the solvent
customgave a residue, which
customwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1)

出典と根拠

ORDレコード: ord-7979378220074b7c996aa06eafdcf99f
出典データセット: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07737163B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

関連ノート