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

HRID 1247477Notes

Reaction equation

HRID 1247477 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3c90b40a48844ea4a1cbab1396682c44
Source dataset
uspto-grants-2006_10
Patent number
US07129262B2

Reaction notes

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