trans-3-hydroxy-L-proline → 1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

HRID 751129노트

반응식

HRID 751129 반응식
C[O:2][C:3]([C@@H:5]1[C@H:9]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:8][CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O.O[C@H]1CCN[C@@H]1C(O)=O.COC(=O)[C@@H]1[C@@H](O[Si](C(C)(C)C)(C)C)CCN1C(OC(C)(C)C)=O.C([BH-](CC)CC)C.[Li+]>C1COCC1>[C:21]([O:20][C:18]([N:6]1[CH2:7][CH2:8][C@H:9]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C@H:5]1[CH2:3][OH:2])=[O:19])([CH3:24])([CH3:23])[CH3:22]

참가 물질

6

반응물 4

HCID 440575trans-3-hydroxy-L-prolineHCID 23664628LithiumtriethylborohydrideHCID 58841066Methyl (2S,3S)-1-Boc-3-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylateHCID 68455583(2S,3R)-3-(tert-Butyldimethylsilanyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Following procedures described for the preparation of (2S,3R)—N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)proline methyl ester (51A), (2S,3S)-3-hydroxyproline was converted to (2S,3S)—N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)proline methyl ester. To this material (4.3 g, 12 mmol) in THF (75 mL) at −78° C. under nitrogen was added dropwise 1.0 M lithium triethylborohydride in THF (60 mL, 60 mmol). The reaction was allowed to warm to rt and was stirred for 4 h. The reaction was quenched by pouring over ice (150 g) and stirring for 30 min. The product was extracted into EtOAc and washed with saturated aqueous NaHCO3. The organics were dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica gel, 0-15% EtOAc in hexanes) provided the title compound (3.3 g). 61B. (2S,3S)—N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-formyl-pyrrolidine

후처리

  1. customThe reaction was quenched
  2. additionby pouring over ice (150 g)
  3. stirringstirring for 30 min
  4. extractionThe product was extracted into EtOAc
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (silica gel, 0-15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-6bfa9c412c564be2bcdfd30146a2ca09
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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