Hydrochloric Acid → (R)-(2-adamantyl) 3-(isobutoxycarbonylamino)pyrrolidine-1-carboxylate

HRID 72132

反応式

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]2[CH:24]3[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:26][CH:18]2[CH2:19]4)[CH2:23]3)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27]I.[H-].[Na+].Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH3:27])[CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]2[CH:18]3[CH2:19][CH:20]4[CH2:21][CH:22]([CH2:23][CH:24]2[CH2:25]4)[CH2:26]3)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[CH2:2]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]2[CH:24]3[CH2:23][CH:22]4[CH2:21][CH:20]([CH2:19][CH:18]2[CH2:26]4)[CH2:25]3)=[O:15])[CH2:10]1)=[O:7])[CH:1]([CH3:4])[CH3:3]

参加物

反応条件

温度: 50 °C

実験手順

2-adamantyl 3-(tert-butoxycarbonyl(methyl)amino)pyrrolidine-1-carboxylate was prepared as follows. A vial equipped with a flea stirbar was charged with (3R)-(2-adamantyl) 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate (105 mg, 0.29 mmol), methyl iodide (36 μL, 0.58 mmol) and dry THF (1 mL). 60% NaH in oil (14 mg, 0.58 mmol) was added and the mixture was stirred overnight under N2. The mixture was heated at 50° C. for 1 h, cooled and applied to a 10-mL ChemElut cartridge, prewetted with 5% aq HCl (6 mL), and eluted with ether (20 mL). The eluate was concentrated and the residue was purified by preparative HPLC to afford (R) 2-adamantyl 3-(tert-butoxycarbonyl(methyl)amino)pyrrolidine-1-carboxylate (32 mg, 29%).

後処理

customA vial equipped with a flea stirbar
temperaturecooled
washeluted with ether (20 mL)
concentrationThe eluate was concentrated
customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード: ord-bbaa93a5146b4d9d9957605f7bea428c
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08828985B2

反応式

参加物

反応物 4

生成物 2

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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