(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehyde → 1-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-propan-2-ol

HRID 901064ノート

反応式

HRID 901064 の反応式
[CH2:1]([C:3]1([CH2:18][CH:19]=[O:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].[CH3:21][Mg]Cl>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([C:3]1([CH2:18][CH:19]([OH:20])[CH3:21])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2]

参加物

5

反応物 2

HCID 20516149(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehydeHCID 178418332HCID 178418332、化合物2 回

生成物 1

HCID 219075771-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-propan-2-ol収率 96%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of compound 8 (275 mg, 1.01 mmol) in dry THF (4 mL) was added dropwise over five minutes to a stirred solution of 1M MeMgCl in THF (1.52 mL, 1.52 mmol, 1.5 eq) at 0° C. under argon and allowed to warm slowly to room temperature. After stirring for two hours, another equivalent of 3M MeMgCl in THF (337 μL, 1.01 mmol, 1.0 eq) was added, and the mixture was stirred for an additional hour. The mixture was then diluted with saturated NaHCO3 and extracted three times with EtOAc. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 20:80:EtOAc:Hexane to give a yellow solid (280 mg, 96%): mp 103-104° C. 1HNMR (CDCl3, δ TMS) shows a 2:1 mixture of diastereomers. MS−: m/z 322 (MCl−), 286 ([M−H]−). Anal. (C18H25NO2): C, H, N. The product was carried on to the next step as a mixture of diastereomers.

後処理

  1. stirringthe mixture was stirred for an additional hour
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography

出典と根拠

ORDレコード
ord-36f234b01bec4cdea209f9e935176d98
出典データセット
uspto-grants-2008_04
特許番号
US07361680B2

反応ノート

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