Toluene → HCID 46831040, compound

HRID 446206Notes

Reaction equation

HRID 446206 reaction equation
[CH2:1]([O:3][C:4]([C:6]12[CH2:13][CH2:12][C:9]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([CH2:10][CH2:11]1)[CH2:8][CH:7]2[OH:22])=[O:5])[CH3:2].C1(C)C=CC=CC=1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]12[CH2:13][CH2:12][C:9]([NH:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([CH2:10][CH2:11]1)[CH2:8][CH:7]2[O:22][S:38]([CH3:37])(=[O:40])=[O:39])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46831039Ethyl 2-hydroxy-4-[(phenylmethyl)amino]bicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 46831040HCID 46831040, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(benzylamino)-2-hydroxybicyclo[2.2.2]octane-1-carboxylic acid ethyl ester (6.0 g, 19.8 mmol), there were added toluene (42.0 g), tetrahydrofuran (10.8 g) and triethylamine (4.0 g, 39.6 mmol) and then the resulting mixture was stirred. Methanesulfonyl chloride (2.9 g, 24.9 mmol) was added dropwise to the mixture, followed by the stirring thereof for one hour and 30 minutes. After quenching the reaction mixture with water, the resulting mixture was subjected to extraction procedures and the organic phase was quantitatively analyzed (according to the LC technique). As a result, the yield of the desired product was found to be 100% (the internal standard substance used was m-xylene).

Workup

  1. customfor one hour
  2. custom30 minutes
  3. customAfter quenching the reaction mixture with water
  4. extractionthe resulting mixture was subjected to extraction procedures

Sources & evidence

ORD record
ord-5588399d70194e329514ba6a3af8e13e
Source dataset
uspto-grants-2013_07
Patent number
US08476470B2

Reaction notes

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