Dimethyl Sulfoxide → HCID 21907578, compound

HRID 901063Notes

Reaction equation

HRID 901063 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=[O:7].[CH2:11]([C:13]1([CH2:28][CH2:29][OH:30])[C:18]2[NH:19][C:20]3[C:25]([C:17]=2[CH2:16][CH2:15][O:14]1)=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][CH3:27])[CH3:12]>C(Cl)Cl.[NH4+].[Cl-]>[CH2:11]([C:13]1([CH2:28][CH:29]([OH:7])[OH:30])[C:18]2[NH:19][C:20]3[C:25]([C:17]=2[CH2:16][CH2:15][O:14]1)=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][CH3:27])[CH3:12]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

Product 1

HCID 21907578HCID 21907578, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

Dry DMSO (71 μL, 1.0 mmol, 2.0 eq) was added dropwise to a solution of oxalyl chloride (66 μL, 0.75 mmol, 1.5 eq) in CH2Cl2 (1 mL) at −78° C. After stirring for ten minutes, a solution of compound 1 (136 μL, 0.5 mmol) in CH2Cl2 (4 mL) was added dropwise, and the reaction was stirred for an additional thirty minutes at −78° C. before the addition of TEA (2.79 μL, 2.0 mmol, 4.0 eq). The reaction mixture was then allowed to warn slowly to 0° C., diluted with saturated NH4Cl, and extracted twice with Et2O. The combined organic phases were washed with water and brine, dried with Na2SO4, concentrated, and purified by column chromatography using a gradient of 50:50:EtOAc:Hexane to 100% EtOAc to give a white solid (46 mg, 32%): mp 158-159° C. 1HNMR (CDCl3, δ TMS): 0.50 (t, 3H), 1.25 (t, 3H), 1.50 (m, 1H), 1.82 (m, 1H), 2.04 (m, 1H), 2.17 (m, 1H), 2.33 (m, 1H), 2.58 (q, 2H), 2.88 (m, 2H), 3.77 (m, 1H), 3.91 (m, 1H), 4.19 (q, 1H), 4.33 (m, 1H), 7.02-7.15 (m, 3H, Ar—H), 7.66 (br, 1H, NH). MS−: m/z 288 ([M−H]−). Anal. (C17H23NO3): C, H, N.

Workup

  1. customto warn slowly to 0° C.
  2. extractionextracted twice with Et2O
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-e7c838e0c5ea4c86aeef0a32609a9c44
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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