Chlorosulfonic acid → HCID 86590895, compound

HRID 1670366Notes

Reaction equation

HRID 1670366 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[CH2:6]([O:16][CH2:17][CH:18]([OH:30])[CH2:19][N:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[CH2:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][CH2:29][N:20]1[CH2:19][CH:18]([O:30][S:2](=[O:4])(=[O:3])[OH:5])[CH2:17][O:16][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 67336992HCID 67336992, compound

Product 1

HCID 86590895HCID 86590895, compound

Procedure

2-Decyloxymethyl-oxirane (1 equiv.), prepared according to Example 1 (except 1-decanol is substituted for 2-ethylhexanol), is dissolved in acetonitrile and warmed to 70° C. Stannic chloride (0.1 equiv.) is added to the reaction, which is maintained at 70° C. with stirring for 24-48 hours to give the oxazolidine. The reaction is cooled to from about 20° C. to about 25° C. and chlorosulfonic acid (1 equiv.) is added to the reaction at a temperature of from about 20° C. to about 25° C. to yield the product, through sulfation of the putative intermediate 1-Decyloxy-3-(3,4-dihydro-isoquinolin-2-yl)-propan-2-ol.

Workup

  1. additionis added to the reaction at a temperature of from about 20° C. to about 25° C.
  2. customto yield the product

Sources & evidence

ORD record
ord-40f73337b8de4f74aed5a756dd83abcb
Source dataset
uspto-grants-2011_08
Patent number
US07994109B2

Reaction notes

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