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

HRID 924424노트

반응식

HRID 924424 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

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온도
0 °C

실험 절차

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 Et2O and 1 M NaOH was added. The resulting mixture was extracted with EtOAc. The separated organic extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with 0-20% EtOAc in hexanes) to give the sub-title compound (1.2 g, 78%). LCMS calc. for C15H34NO3Si (M+H-Boc)+: m/z=304.2. found 304.2.

후처리

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

출처 및 근거

ORD 기록
ord-4bba70857d5843818dc445dae103b2a8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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