Methyl 6-chloro-5-nitronicotinate → (S)-methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinate

HRID 716249

反応式

HRID 716249 の反応式
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([O:23][CH3:24])=[O:22]>C(OCC)(=O)C>[CH3:24][O:23][C:21]([C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)=[O:22]

参加物

4

反応物 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 853680(S)-Methyl piperidine-2-carboxylate

生成物 1

HCID 58324510(S)-methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinate収率 98%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Methyl 6-chloro-5-nitronicotinate (2.333 g, 10.77 mmol) was added to (S)-methyl piperidine-2-carboxylate (2.93 g, 20.46 mmol) neat while stirring. The reaction was stirred 1 h at 90° C., cooled to room temperature and taken up in ethyl acetate (10 mL). The mixture was purified by SiO2 (330 g, 20-30% EA in Hexanes) to yield 3.4 g (98%) of the title compound as a yellow oil. [M+H] calc'd for C14H17N3O6, 324. found, 324.

後処理

  1. stirringThe reaction was stirred 1 h at 90° C.
  2. customThe mixture was purified by SiO2 (330 g, 20-30% EA in Hexanes)

出典と根拠

ORDレコード
ord-171d7b0e727a4bedba22c16fa5ff3629
出典データセット
uspto-grants-2015_11
特許番号
US09187497B2

関連ノート

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