Tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxy-pyrrolidine-1-carboxylate → HCID 68465076、化合物

HRID 732276

反応式

HRID 732276 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12]([N:14]1[CH2:18][CH:17]([OH:19])[CH:16]([NH:20][C:21](OCC2C=CC=CC=2)=O)[CH2:15]1)=O)(C)(C)C>C1COCC1>[CH3:12][N:14]1[CH2:15][CH:16]([NH:20][CH3:21])[CH:17]([OH:19])[CH2:18]1

参加物

4

反応物 2

HCID 20691380Tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxy-pyrrolidine-1-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 68465076HCID 68465076、化合物収率 18%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

LAH (1.40 g, 35.0 mmol) is slowly added to a stirred solution of 3-benzyloxycarbonylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester in THF (15 ml) at room temperature. The reaction mixture is heated to reflux under N2 for 2 hours and then cooled to 0° C. The reaction mixture is quenched by the slow addition of Na2SO4.10H2O, warmed to room temperature, diluted with ethyl acetate and filtered through Celite. The filtrate is concentrated and purified on a silica gel column (10:1:0.5 methylene chloride, MeOH, 30% NH4OH solution) to yield 0.21 g (18% for two steps) 1-methyl-4-methylamino-pyrrolidin-3-ol.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under N2 for 2 hours
  3. customThe reaction mixture is quenched by the slow addition of Na2SO4.10H2O
  4. temperaturewarmed to room temperature
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate is concentrated
  8. custompurified on a silica gel column (10:1:0.5 methylene chloride, MeOH, 30% NH4OH solution)

出典と根拠

ORDレコード
ord-517b1a151371432f8a873afce9e63243
出典データセット
uspto-grants-2009_09
特許番号
US07585975B2

関連ノート

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