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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0

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反応

Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)amino]-, phenylmethyl ester, (2S,5R)-

HRID 508452

印刷プレビュー

反応式

HRID 508452 の反応式

C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH2:16]([O:23][C:24]([C@@H:26]1[CH2:31][CH2:30][C:29](=[N:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:28][NH:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.B.O1CCCC1>O1CCCC1>[CH2:16]([O:23][C:24]([C@@H:26]1[CH2:31][CH2:30][C@@H:29]([NH:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:28][NH:27]1)=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物反応条件実験手順出典と根拠反応ノート

参加物

5

反応物 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

HCID 2723981Borane;tetrahydrofuran

HCID 86702281Phenylmethyl (2S)-5-[(phenylmethoxy)imino]-2-piperidinecarboxylate

生成物 1

HCID 706739342-Piperidinecarboxylic acid, 5-[(phenylmethoxy)amino]-, phenylmethyl ester, (2S,5R)-収率 82.3%

試薬・触媒・溶媒 1

HCID 8028

Tetrahydrofuran

溶媒

反応条件

温度: -20 °C

実験手順

Under nitrogen atmosphere, (±)-camphorsulfonic acid (0.697 g, 3.00 mmol) and tetrahydrofuran (2 ml) was added to (2S)-5-benzyloxyimino-piperidine-2-carboxylic acid benzyl ester (0.169 g, 0.50 mmol), and the mixture was cooled down to −20° C. Borane-tetrahydrofuran complex (1.06 M tetrahydrofuran solution, 2.4 ml, 2.54 mmol) was added to the mixture for 1.5 hours, and the obtained mixture was stirred for 6 hours. The reaction mixture was analyzed with high performance liquid chromatography to find that the reaction mixture contained 0.140 g of the title compound, and the reduction reaction proceeded with yield of 82%. The diastereo selectivity was (2S,5R)/(2S,5S)=87.8/12.2 (75.6% de).

出典と根拠

ORDレコード: ord-06368c262d864600b0d9fc8a31bcdfaa
出典データセット: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09096523B2

反応ノート

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