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

HRID 901065Notes

Reaction equation

HRID 901065 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-8b24d7c574c24343ba4c731ab47a523a
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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