Benzyl Bromide → Diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate

HRID 888211노트

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HRID 888211 반응식
[CH:1]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[OH:7])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH4+].[Cl-]>C1COCC1.O>[CH2:26]([C@H:8]([C@H:6]([OH:7])[C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:15])[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 11333435Diisopropyl (S)-(-)-malate

생성물 1

HCID 14264444Diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate수율 42.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
20 °C

실험 절차

To a cold (−78° C.) solution of diisopropyl-(S)-(−)-malate (4.72 mL, 22.9 mmol, 1 eq.) in anhydrous THF (8.50 mL) was added slowly a solution (1 M) of lithium bis(trimethylsilyl)amide (48.1 mL, 48.1 eq., 2.10 eq.) in tetrahydrofuran. The temperature was raised to 20° C. over 30 minutes, than lowered again to −78° C. Benzyl bromide (4.70 g; 27.5 mmol; 1.20 eq.) was added and the mixture stirred at RT for 16 hours. The reaction mixture was then cooled to 0° C. and a saturated solution of NH4Cl was added. The resulting mixture was diluted with water, extracted three times with EtOAc. The combined organic layers were washed with brine and dried over MgSO4, filtered and evaporated under reduced pressure. The residue was then purified by chromatography (SiO2, 20/80 EtOAc/c-hex) to give the product as a colourless oil (3.00 g, 42%).

후처리

  1. customthan lowered again to −78° C
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. extractionextracted three times with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was then purified by chromatography (SiO2, 20/80 EtOAc/c-hex)

출처 및 근거

ORD 기록
ord-c3d53335d30a4a4687a146a7be2d6f73
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247437B2

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