Dimethyl Sulfoxide → HCID 22246406, compound

HRID 1384388Notes

Reaction equation

HRID 1384388 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:24]=2)[C:20]([CH2:38][OH:39])([CH3:37])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[CH:24]=2)[C:20]([CH3:37])([CH:38]=[O:39])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22246558HCID 22246558, compound

Product 1

HCID 22246406HCID 22246406, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (4.87 mL, 9.73 mmol) in dry CH2Cl2 (20 mL) was chilled to −78° C. under N2 and stirred while being treated with a solution of dimethyl sulfoxide (DMSO, 1.38 mL, 19.5 mmol) in CH2Cl2 (5 mL). Gas evolution was observed. When addition was complete, the solution was stirred for 5 minutes and a solution of [1-benzyl-4-(3-cyclopentyloxy-4-methyoxy-phenyl)-3-methylpyrrolidin-3-yl]-methanol (3.5 g, 8.85 mmol) in CH2Cl2 (10 mL) was added over a period of 10 minutes. The mixture was stirred for 30 minutes, treated with triethylamine (6.7 mL, 44.3 mmol), and allowed to warm to room temperature. Water was added to the mixture, the resulting layers separated, and the aqueous layer extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give an oily product (3.2 g, 92% yield). 1H NMR (300 MGz, CDCl3) δ (ppm): 9.63 (s, 1H, CHO), 7.34-7.21 (m, 5H, aromatic), 6.78-6.68 (m, 3H, aromatic), 4.73 (br, m, 1H), 3.80 (s, 3H, OCH3), 3.78-3.61 (m, 3H), 3.18-3.11 (m, 2H), 2.86-2.81 (m, 1H), 2.58-2.52 (m, 1H), 2.43-2.34 (m, 2H), 1.87-1.59 (m, 8H, cyclopentyl), 0.74 (s, 3H, CH3)

Workup

  1. additionWhen addition
  2. stirringthe solution was stirred for 5 minutes
  3. stirringThe mixture was stirred for 30 minutes
  4. customthe resulting layers separated
  5. extractionthe aqueous layer extracted with CH2Cl2 (2×50 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-572be43489034d8f88da698353e16e2e
Source dataset
uspto-grants-2001_07
Patent number
US06258833B1

Reaction notes

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