Dimethyl Sulfoxide → HCID 21055337, compound

HRID 2215267Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C@H:12]([CH2:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:13][OH:14].C(N(CC)CC)C>ClCCl>[CH3:11][C@H:12]([CH2:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH:13]=[O:14]

Participants

Conditions

Temperature: -78 °C

Procedure

0.61 ml (0.007 mol) of oxalyl chloride and 20 ml of dichloromethane are introduced into a round-bottomed flask kept under an inert atmosphere. The mixture is cooled to −78° C. and then 1 ml (0.014 mol) of dimethyl sulfoxide is introduced. After stirring at −78° C. for 15 minutes, 1.5 g (0.007 mol) of 2-(S)-methyl-3-(2-methoxyphenylthio)propan-1-ol (XXb-1), in solution in 15 ml of dichloromethane, are added dropwise. The mixture is stirred at −78° C. for 1 hour and then 2 ml (0.014 mol) of triethylamine are added. After 15 minutes at −78° C., the mixture is reheated to −10° C. and stirred at this temperature for 45 minutes. The aldehyde is not isolated at this stage but is used in situ in the following reductive amination reaction.

Workup

stirringThe mixture is stirred at −78° C. for 1 hour
waitAfter 15 minutes at −78° C.
customis reheated to −10° C.
stirringstirred at this temperature for 45 minutes

Sources & evidence

ORD record: ord-00f05abf1fc14658bf3ae5f3c71bee50
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109234B2

Reaction notes

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