Diethyl Ether → HCID 18381537, compound

HRID 2298094Notes

Reaction equation

HRID 2298094 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(OCC)C>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]=[O:24])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:5]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 18381564HCID 18381564, compound

Product 1

HCID 18381537HCID 18381537, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-chloro-5-(2-hydroxyethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (1.07 g, Example 66a) in anhydrous dichloromethane (20 ml) was added Dess-Martin periodinane reagent (1.95 g) and the mixture was stirred at room temperature for 1 h. Sodium thiosulfate (3.43 g) was dissolved in aqueous sodium bicarbonate solution (28 ml) and added to the reaction mixture. Diethyl ether (50 ml) was then added and the mixture was stirred for 10 min. The layers were partitioned and the organic layer was washed with water then brine. The organic extracts were then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the subtitle compound as a white solid (1.06 g).

Workup

  1. additionadded to the reaction mixture
  2. stirringthe mixture was stirred for 10 min
  3. customThe layers were partitioned
  4. washthe organic layer was washed with water
  5. dry with materialThe organic extracts were then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a5c422348944f578e0ae302f1cee044
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

Loading…