(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 901064노트

반응식

HRID 901064 반응식
[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]

참가 물질

5

반응물 2

HCID 20516149(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehydeHCID 178418332HCID 178418332, 화합물2회

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-36f234b01bec4cdea209f9e935176d98
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361680B2

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