Water → trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1666673ノート

反応式

HRID 1666673 の反応式
C([O:4][C@H:5]1[C@H:9]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:8][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:14]([O:13][C:11]([NH:10][C@H:9]1[C@H:5]([OH:4])[CH2:6][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8]1)=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57970174t-Butyl (3R,4R)-3-acetoxy-4-benzyloxycarbonylaminopyrrolidine-1-carboxylate

生成物 1

HCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate収率 91.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

t-Butyl (3R,4R)-3-acetoxy-4-benzyloxycarbonylaminopyrrolidine-1-carboxylate (27 g) was dissolved in methanol (350 mL), followed by addition of potassium carbonate (16 g) with ice cooling, and the mixture was stirred overnight at room temperature. Water was added, and then the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1-2:1) to obtain t-butyl (3R,4R)-3-benzyloxycarbonylamino-4-hydroxypyrrolidine-1-carboxylate (22 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1-2:1)

出典と根拠

ORDレコード
ord-5ece42eb747f405baec5313a3bff91f9
出典データセット
uspto-grants-2011_10
特許番号
US08044068B2

反応ノート

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