Hydrochloric Acid → Allyl-((R)-1-methyl-pent-4-enyl)-carbamic acid benzyl ester

HRID 229801노트

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HRID 229801 반응식
[CH2:1]([O:8][C:9](=[O:17])[NH:10][C@H:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22].Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:17])[N:10]([CH2:22][CH:21]=[CH2:20])[C@H:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 11107239(R)-(1-Methyl-pent-4-enyl)-carbamic acid benzyl ester

생성물 1

HCID 58665071Allyl-((R)-1-methyl-pent-4-enyl)-carbamic acid benzyl ester수율 95.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

((R)-1-Methyl-pent-4-enyl)-carbamic acid benzyl ester (790 mg, 3.39 mmol) was dissolved in DMF (8 ml) and was cooled to 0 degrees C. Sodium hydride (60% dispersion, 271 mg, 6.78 mmol) was added and the reaction was stirred for 15 minutes. Allyl bromide (1.23 g, 0.88 ml, 10.17 mmol) was added and the reaction mixture was stirred for 3 h at 0 degrees C. H2O (10 ml) was added, then 2N HCl was added dropwise adjusting the pH to 1. The reaction mixture was extracted with Et2O (2×50 ml). The combined organics were washed with aq. 2N HCl, then aq. NaHCO3, then brine. The combined organics were dried with MgSO4, filtered, concentrated in vacuo, then chromatographed on silica gel (5% EtOAc/hexanes) to yield the title compound as a colorless oil (883 mg, 95%).

후처리

  1. stirringthe reaction mixture was stirred for 3 h at 0 degrees C
  2. extractionThe reaction mixture was extracted with Et2O (2×50 ml)
  3. washThe combined organics were washed with aq. 2N HCl
  4. dry with materialThe combined organics were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed on silica gel (5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-6d06fa7b657242069e2098de16eca957
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563784B2

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