Lithium hydroxide, monohydrate → (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid

HRID 1424673ノート

反応式

HRID 1424673 の反応式
[CH2:1]1[C:3]2([CH2:7][C@@H:6]([C:8]([O:10]C)=[O:9])[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]2)[CH2:2]1.O[Li].O>C(O)C.O>[C:15]([O:14][C:12]([N:5]1[C@H:6]([C:8]([OH:10])=[O:9])[CH2:7][C:3]2([CH2:2][CH2:1]2)[CH2:4]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 57611019(S)-5-tert-Butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate

生成物 1

HCID 39871141(6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid収率 102.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of (S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate (0.436 g, 1.708 mmol) in ethanol (4 mL) was added a solution of LiOH.H2O (86.0 mg, 2.049 mmol, 1.2 eq) in H2O (2 mL) at room temperature. The mixture was stirred at room temperature for 20 hours. EtOH was removed by rotavapor. The aqueous residue was diluted with H2O and extracted with Et2O. The aqueous layer was cooled with an ice bath and acidified to pH ˜2 with 1 N HCl. The resulting milky solution was extracted with a mixed solvent of EtOAc and CH2Cl2. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was dried under vacuum to afford the desired product as an off-white solid (0.422 g, 100%).

後処理

  1. customEtOH was removed by rotavapor
  2. additionThe aqueous residue was diluted with H2O
  3. extractionextracted with Et2O
  4. temperatureThe aqueous layer was cooled with an ice bath
  5. extractionThe resulting milky solution was extracted with a mixed solvent of EtOAc and CH2Cl2
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was dried under vacuum

出典と根拠

ORDレコード
ord-c274e61221014342aff2189a69d50366
出典データセット
uspto-grants-2015_01
特許番号
US08927739B2

反応ノート

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