Ethanol → (R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1499469ノート

反応式

HRID 1499469 の反応式
[Li+].[BH4-].C([C@@H]1COC(=O)N1[C:16](=[O:42])[C@H:17]([CH3:41])[C@H:18]([C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])C1C=CC=CC=1.CCO>C1COCC1.CCOCC.[OH-].[Na+]>[Si:20]([O:19][C@@H:18]([C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@@H:17]([CH3:41])[CH2:16][OH:42])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:22])[CH3:21]

参加物

7

反応物 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 68547408(R)-tert-butyl 4-((1R,2R)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(tert-butyldimethylsilyloxy)-2-methyl-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

生成物 1

HCID 59226545(R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate収率 78.2%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

LiBH4 (0.25 g, 11 mmol) was added to a mixture of tert-butyl (4R)-4-((1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (2.2 g, 3.8 mmol) and EtOH (0.67 mL, 11 mmol) in THF (40 mL) at −30° C. The mixture was allowed to warm to 0° C. and stirred for 3 h. The reaction mixture was then diluted with ether and 1N NaOH was added. The resulting mixture was extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-20% EtOAc in hexanes) to afford the sub-title compound (1.2 g, 78%). LCMS calc. for C15H34NO3Si (M+H-Boc)+: m/z=304.2. found 304.2.

後処理

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (0-20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-eee0cb86f94f444ca75c5aa23d2afc2d
出典データセット
uspto-grants-2015_12
特許番号
US09200004B2

反応ノート

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