Dimethyl Sulfoxide → HCID 19697711, compound

HRID 863224Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH:20]([CH:28]([OH:30])[CH3:29])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.C(N(CC)CC)C>[CH2:11]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH:20]([C:28](=[O:30])[CH3:29])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -65 °C

Procedure

0.78 ml of oxalyl chloride is dissolved in 15 ml of methylene chloride and the solution is cooled to -65° C. First 0.85 ml of dimethyl sulfoxide and then a solution 1.6 g of 1-benzyl-3(R,S)-(1-hydroxyethyl)-1,2,3,4-tetrahydroquinoline and 3.3 ml of triethylamine in 25 ml of methylene chloride are added dropwise at this temperature. After 3 h, 10 ml of a 20% potassium hydrogen sulfate solution are added. The crude product is extracted with methylene chloride and purified by means of FC over 500 g of silica gel (mobile phase D): Rf (D)=0.27.

Workup

extractionThe crude product is extracted with methylene chloride
custompurified by means of FC over 500 g of silica gel (mobile phase D)

Sources & evidence

ORD record: ord-8f9131e7b8f44b5fa376fca2b4726c59
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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