Acetic Acid → HCID 57054788、化合物

HRID 1078719ノート

反応式

HRID 1078719 の反応式
C[O:2][C:3](=[O:21])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[Cl-].[Li+].[BH4-].[Na+].[C:26](O)(=[O:28])C>O1CCCC1CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([N:5]1[CH2:6][C@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:8][C@:4]1([CH2:26][OH:28])[C:3]([OH:2])=[O:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 57054788HCID 57054788、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 7360Tetrahydrofurfuryl alcohol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxyproline methyl ester (10.0 g, 30.9 mmol) in tetrahydrofuran--methanol (1:1, 100 ml) were successively added lithium chloride (3.93 g, 92.8 mmol) and sodium borohydride (3.51 g, 92.8 mmol). The reaction solution was stirred at room temperature for 11 h. Acetic acid (2 ml) was added to the reaction solution, and ethyl acetate and water were added thereto. The mixture was concentrated in vacuo. The residue was dissolved in water and ethyl acetate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to obtain a residue of (2S,4R)-N-tert-butoxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxyproline (9.41 g).

後処理

  1. additionwere added
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionethyl acetate and extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-9853c9091ad24a42995e6ad36451466c
出典データセット
uspto-grants-1996_08
特許番号
US05550121

反応ノート

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