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

HRID 1677770노트

반응식

HRID 1677770 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

반응 조건

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-58d15b5f25724a37a6a5721fb54ff49b
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008302B2

반응 노트

불러오는 중…