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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

Sulfuric Acid → 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)amino]-, phenylmethyl ester, (2S,5R)-

HRID 508453

印刷プレビュー

反応式

HRID 508453 の反応式

S(=O)(=O)(O)O.[BH4-].[Na+].[CH2:8]([O:15][C:16]([C@@H:18]1[CH2:23][CH2:22][C:21](=[N:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:20][NH:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>O1CCCC1>[CH2:8]([O:15][C:16]([C@@H:18]1[CH2:23][CH2:22][C@@H:21]([NH:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:20][NH:19]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1118Sulfuric Acid

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

HCID 4311764Sodium borohydride

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 74%

試薬・触媒・溶媒

1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under nitrogen atmosphere, tetrahydrofuran (3 ml) and sulfuric acid (0.151 g, 1.53 mmol) were added to sodium borohydride (0.101 g, 2.66 mmol). The obtained mixture was added dropwise at −10° C. to the mixture consisting of (2S)-5-benzyloxyimino-piperidine-2-carboxylic acid benzyl ester (0.168 g, 0.50 mmol), (+)-camphorsulfonic acid (0.695 g, 2.99 mmol) and tetrahydrofuran (2 ml) for 0.5 hour. After 22 hours of stirring, the obtained reaction mixture was analyzed with high performance liquid chromatography to find that the reaction mixture contained 0.125 g of the title compound, and the reduction reaction proceeded with yield of 74%. The diastereo selectivity was (2S,5R)/(2S,5S)=81.4/18.6 (62.8% de).

後処理

additionThe obtained mixture was added dropwise at −10° C. to the mixture
customthe obtained reaction mixture

出典と根拠

ORDレコード: ord-bec93985e49343e5bd4a5c757b75540b
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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