Lithium aluminum hydride → 6-[(3-Chloro-pyridin-4-ylmethyl)-amino]pyridin-3-yl-methanol

HRID 1024259ノート

反応式

HRID 1024259 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[Cl:18])=[N:6][CH:5]=1.[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:18][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][C:7]1[N:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 28112Lithium aluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 576192956-[(3-Chloro-pyridin-4-ylmethyl)-amino]-nicotinic acid methyl ester

生成物 1

HCID 576192366-[(3-Chloro-pyridin-4-ylmethyl)-amino]pyridin-3-yl-methanol収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 6-[(3-chloro-pyridin-4-ylmethyl)-amino]-nicotinic acid methyl ester (555, 1.00 g, 3.60 mmol) in tetrahydrofuran (120 mL) was added a solution of lithium tetrahydroaluminate (1.00M in tetrahydrofuran, 5.00 mL) under an atmosphere of nitrogen at room temperature. The reaction was stirred at room temperature overnight, followed with addition of sodium sulfate decahydrate. After 1 hour, the reaction mixture was filtered, concentrated, and purified with silica gel column chromatography eluting with 2% to 20% methanol in dichloromethane to give the desired compound as a white solid (556, 0.5 g, 56%). MS (ESI) [M+H+]+=250.1.

後処理

  1. waitAfter 1 hour
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 2% to 20% methanol in dichloromethane

出典と根拠

ORDレコード
ord-7a72b6f7747e4d859a29f132045db877
出典データセット
uspto-grants-2014_05
特許番号
US08722702B2

反応ノート

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