Sodium borohydride → Tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylate

HRID 2403605ノート

反応式

HRID 2403605 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[O:22])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][OH:22])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 86667973Tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 68107347Tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylate収率 91.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylate (1 g) and MeOH (20 ml) was added sodium borohydride (153 mg). After stirring at room temperature for 2 hours, the solvent was evaporated under reduced pressure. To the obtained residue was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl 4-[5-bromo-3-(hydroxymethyl)pyridin-2-yl]piperazine-1-carboxylate (922 mg).

後処理

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the obtained residue was added water
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-28a9f422bc034dd9b795f3e0b9308502
出典データセット
uspto-grants-2014_08
特許番号
US08802679B2

反応ノート

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