Water → (1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol

HRID 988114ノート

反応式

HRID 988114 の反応式
[C:1]1([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]2Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>CO>[C:1]1([CH2:7][N:8]2[CH2:9][CH:10]=[C:11]([CH2:14][OH:15])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22708810HCID 22708810、化合物

生成物 1

HCID 11264156(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol収率 87.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
-20 °C

実験手順

1-(Phenylmethyl)-4-(hydroxymethyl)-pyridinyl chloride(0.87 mol) was dissolved in methanol (2200 ml) and cooled to −20° C. Sodium borohydride (1.75 mol) was added portionwise under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes and water (200 ml) was added dropwise. The reaction mixture was partially evaporated, water was added and the reaction mixture was extracted with DCM. The organic layer was separated, dried, filtered and evaporated. The residue was purified over silica gel (eluent: DCM), yielding 155 g 1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol.

後処理

  1. customThe reaction mixture was partially evaporated
  2. additionwater was added
  3. extractionthe reaction mixture was extracted with DCM
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified over silica gel (eluent: DCM)

出典と根拠

ORDレコード
ord-107a591f7a434662bdd3531a54e58e04
出典データセット
uspto-grants-2003_10
特許番号
US06635643B2

反応ノート

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