Dimethyl Sulfoxide → HCID 21907571, compound

HRID 901062Notes

Reaction equation

HRID 901062 reaction equation
[CH2:1]([C:3]1([CH2:18][CH2:19][OH: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].CS(C)=O.[CH3:25][C:26](OC(C)=O)=[O:27]>O>[CH2:1]([C:3]1([CH2:18][CH2:19][O:20][C:26](=[O:27])[CH3:25])[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

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

Product 1

HCID 21907571HCID 21907571, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of compound 1 (273 mg, 1.0 mmol), dry DMSO (3 mL), dry Ac2O (2 mL), and dry TEA (1 mL) was stirred overnight at room temperature. The reaction mixture was then diluted with water and extracted three times with EtOAc. The combined organic phases were washed with saturated NaHCO3 and brine, dried with Na2SO4, concentrated, and purified by column chromatography using 10:90:EtOAc:Hexane to give a yellow solid (245 mg, 78%): mp 126-127° C. 1HNMR (CDCl3, δ TMS): 0.91 (t, 3H), 1.38 (t, 3H), 1.88 (s, 3H), 1.90 (m, 2H), 2.21 (t, 2H), 2.78 (m, 2H), 2.87 (q, 2H), 4.01 (t, 2H), 4.14 (m, 2H), 7.02-7.37 (m, 3H, Ar—H), 7.71 (br, 1H, NH). MS−: m/z 350 (MCl−), 314 ([M−H]−). Anal. (C19H25NO3): C, H, N.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic phases were washed with saturated NaHCO3 and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-0a459a21965744918e2e3e14b7127b95
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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