(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 452011ノート

反応式

HRID 452011 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-4d2f2dacac8e47908caaf420b55d139a
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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