Toluene → 4(S)-t-Butyloxycarbonylamino-5-cyclohexyl-3(R,S)hydroxy-1-pentene

HRID 231085노트

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HRID 231085 반응식
C[O:2][C:3](=O)[C@H:4](C)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1CCCCC1.[H-].C([Al+]CC(C)C)C(C)C.[CH:31]([Mg]Br)=[CH2:32].[C:35]1([CH3:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[C:15]([O:14][C:12]([NH:5][C@@H:4]([CH2:41][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[CH:3]([OH:2])[CH:31]=[CH2:32])=[O:13])([CH3:18])([CH3:17])[CH3:16]

참가 물질

5

반응물 4

HCID 1140Toluene2회HCID 18608575Boc-cyclohexylalanine methyl esterHCID 21225700DiisobutylaluminumhydrideHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 138911064(S)-t-Butyloxycarbonylamino-5-cyclohexyl-3(R,S)hydroxy-1-pentene수율 60%

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온도
0 °C

실험 절차

To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (10.2 g, 35.8 mmol) in dry toluene (60 mL) was added diisobutylaluminum hydride (34 mL of a 1.5M solution in toluene). After 30 minutes, vinyl magnesium bromide (108 mL of 1M solution in THF) was added. After stirring for 15 hours at 0° C., the mixture was carefully quenched with methanol, treated with Rochelle salts (22 mL of saturated aqueous solution in 140 mL H2O), and filtered. After extracting the solids 5 times with ethyl acetate, the extracts and filtrate were combined and the organic phase was washed with brine, dried, filtered, and evaporated to an oil (10.2 g). Chromatography on silica gel eluting with hexane/ethyl acetate mixtures provided 6.1 g (60%) of the desired product.

후처리

  1. customthe mixture was carefully quenched with methanol
  2. additiontreated with Rochelle salts (22 mL of saturated aqueous solution in 140 mL H2O)
  3. filtrationfiltered
  4. extractionAfter extracting the solids 5 times with ethyl acetate
  5. washthe organic phase was washed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated to an oil (10.2 g)

출처 및 근거

ORD 기록
ord-fba2b942c8774b5788ae3fcd1fc95603
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845079

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