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

HRID 1442974노트

반응식

HRID 1442974 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-66b0a28c38ab47c0adcce9286056ef72
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659305B2

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