(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate → tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

HRID 452011노트

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HRID 452011 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@H:14]2[CH2:19][CH2:18][CH2:17][O:16][CH2:15]2)[CH2:11][O:10]C1(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[OH:10][CH2:11][C@@H:12]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][O:16][CH2:15]1

참가 물질

3

반응물 1

HCID 58011520(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate

생성물 1

HCID 58011540tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate수율 79.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
50 °C

실험 절차

(S)-tert-Butyl-2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (9 g, 30.1 mmol) was dissolved in 80% aq CH3CO2H (90 ml). The solution was stirred at 50° C. during 1.5 hr and evaporated to dryness at reduced pressure. The residue was dissolved in Et2O (150 ml) and washed with saturated NaHCO3 (4×100 mL). The organic layer was dried over Na2SO4, filtered, and the solvent removed under reduced pressure to give tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (6.2 g, 79.5%) as an oil, which was used in the next step without further purification.

후처리

  1. customevaporated to dryness at reduced pressure
  2. dissolutionThe residue was dissolved in Et2O (150 ml)
  3. washwashed with saturated NaHCO3 (4×100 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-4d2f2dacac8e47908caaf420b55d139a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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