Dimethyl Sulfoxide → 1-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-propan-2-one

HRID 1247477노트

반응식

HRID 1247477 반응식
[CH2:1]([C:3]1([CH2:18][CH:19]([OH:21])[CH3:20])[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].C(Cl)Cl.CS(C)=O.N1C=CC=CC=1.S(=O)(=O)=O>[Cl-].[Na+].O>[CH2:1]([C:3]1([CH2:18][C:19](=[O:21])[CH3:20])[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]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 168533Sulfur trioxide-pyridineHCID 219075771-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-propan-2-ol

생성물 1

HCID 219075751-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-propan-2-one수율 51%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of compound 12 (77 mg, 0.27 mmol), CH2Cl2 (2 mL), dry DMSO (76 μL, 1.07 mmol, 4.0 eq), and dry TEA (374 μL, 2.68 mmol, 10.0 eq) at room temperature under argon, sulfur trioxide-pyridine complex (Pyr-SO3, 171 mg, 1.07 mmol, 4.0 eq) was added in a portion-wise manner and stirred overnight. The resulting mixture was then diluted with brine and extracted three times with EtOAc. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 15:85:EtOAc:Hexane to give an off-white solid 39 mg, 51%): mp 154–155° C. 1HNMR (CDCl3, δ TMS): 0.80 (t, 3H), 1.37 (t, 3H), 2.02 (m, 2H), 2.21 (s, 3H), 2.78 (m, 2H), 2.88 (q, 2H), 3.14 (s, 2H), 3.98 (m 2H), 7.01–7.37 (m, 3H, Ar—H), 9.01 (br, 1H, NH). MS−: m/z 284 ([M−H]−). Anal. C18H23NO2): C, H, N.

후처리

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-3c90b40a48844ea4a1cbab1396682c44
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129262B2

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