Tetrahydrofuran → HCID 89827530、化合物

HRID 525354ノート

反応式

HRID 525354 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20]1[CH2:24]OCC1.[CH2:25]([Mg]Br)[CH3:26].CCOC(C)=O>CCCCCC>[CH2:20]([C:10]([OH:12])([CH2:25][CH3:26])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:24]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10967413HCID 10967413、化合物HCID 178418443HCID 178418443、化合物

生成物 1

HCID 89827530HCID 89827530、化合物収率 90%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a two-necked 50 mL round bottom flask were added (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate (1.2 g, 5.68 mmol) and dry THF (30 mL). The resulting mixture was cooled to 0° C. Ethyl magnesium bromide (3.02 g, 22.72 mmol) (3M solution in diethyl ether) was added dropwise, and the mixture was slowly allowed to warm to ambient temperature. The mixture was then stirred at ambient temperature for 24 hours. After completion of reaction (monitored by TLC, TLC eluent: 30% EtOAc in hexane), the mixture was quenched in NH4Cl solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated to yield 1.2 g (90.0%) of (R)-tert-butyl (2-ethyl-2-hydroxy-1-phenylbutyl)carbamate as a white solid. 1H NMR (300 MHz, CDCl3) δ: 7.35-7.26 (m, 5H), 5.56 (d, J=9.1 Hz, 1H), 4.61 (d, J=9.4 Hz, 1H), 1.68-1.63 (m, 2H), 1.39 (s, 9H), 1.32-1.22 (m, 2H), 0.92 (t, J=7.4 Hz, 3H), 0.80 (t, J=7.4 Hz, 3H).

後処理

  1. temperatureto warm to ambient temperature
  2. customthe mixture was quenched in NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-21867e90f3524476bdb49cd01e3f4b5e
出典データセット
uspto-grants-2016_05
特許番号
US09340549B2

反応ノート

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