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

HRID 229801ノート

反応式

HRID 229801 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

((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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6d06fa7b657242069e2098de16eca957
出典データセット
uspto-grants-2009_07
特許番号
US07563784B2

反応ノート

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