Borane;tetrahydrofuran → (2S,4S)-4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

HRID 1442974ノート

反応式

HRID 1442974 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10][CH:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][OH:14])[CH2:10][C@H:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:7])([CH3:3])([CH3:4])[CH3:2]

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 68544941Pyrrolidine-1,2,4-tricarboxylic acid 1,2-di-tert-butyl ester

生成物 1

HCID 59166759(2S,4S)-4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester収率 27.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of pyrrolidine-1,2,4-tricarboxylic acid 1,2-di-tert-butyl ester (Preparation 44, 501 mg, 1.59 mmol) in anhydrous tetrahydrofuran (10 ml) at 0° C. under a nitrogen atmosphere was added borane-tetrahydrofuran complex (1M in tetrahydrofuran, 3.16 ml, 3.18 mmol) dropwise and allowed to stir to room temperature over 18 hours. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate (10 ml) and washed with 1M hydrochloric acid (10 ml), saturated sodium hydrogen carbonate (10 ml) and then dried (MgSO4), filtered and evaporated under reduced presssure to give the title compound as a colourless gum (single diastereonier 132 mg, 27%)

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (10 ml)
  3. washwashed with 1M hydrochloric acid (10 ml), saturated sodium hydrogen carbonate (10 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced presssure

出典と根拠

ORDレコード
ord-66b0a28c38ab47c0adcce9286056ef72
出典データセット
uspto-grants-2010_02
特許番号
US07659305B2

反応ノート

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