Sodium borohydride → (2S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627118ノート

反応式

HRID 627118 の反応式
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[C:13](=[O:19])[CH2:12][N:11]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[CH:13]([OH:19])[CH2:12][N:11]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 89852461(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate2 回

生成物 1

HCID 89863076(2S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate) (Intermediate 69, crude, 16.73 g, 43.39 mmol) was dissolved in MeOH (100 mL), cooled to 0° C. and CeCl3 (10.69 g, 43.39 mmol) was added to give a solution. Then NaBH4 (1.642 g, 43.39 mmol) was added slowly as solid, and the mixture was stirred from 0° C. to rt for 30 min. The volatile solvent was removed. The white solid was redissolved in 200 mL EtOAc and washed with sat. NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column (0-100% EA/Hex) to afford 13.78 g, 82% as an colorless oil.

後処理

  1. customto give a solution
  2. customThe volatile solvent was removed
  3. dissolutionThe white solid was redissolved in 200 mL EtOAc
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (0-100% EA/Hex)
  9. customto afford 13.78 g, 82% as an colorless oil

出典と根拠

ORDレコード
ord-e7afff978d214a72962abba6abf91b26
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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