Diisopropylethylamine → (1R)-(-)-N-[2-[[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]amino]ethyl]-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonamide

HRID 893730Notes

Reaction equation

HRID 893730 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH:6]1[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7]1.C(N(C(C)C)CC)(C)C.[CH3:25][C:26]1([CH3:39])[C:30]2([CH2:34][S:35](Cl)(=[O:37])=[O:36])[C:31]([CH2:33][CH:27]1[CH2:28][CH2:29]2)=[O:32]>ClCCl>[O:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7][CH:6]1[CH2:5][NH:4][CH2:3][CH2:2][NH:1][S:35]([CH2:34][C@@:30]12[C:26]([CH3:25])([CH3:39])[CH:27]([CH2:28][CH2:29]1)[CH2:33][C:31]2=[O:32])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 26579910-Camphorsulfonyl chlorideHCID 146529492-[N-(2-aminoethyl)]aminomethyl-2,3-dihydrobenzodioxin

Product 1

HCID 22844791(1R)-(-)-N-[2-[[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]amino]ethyl]-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonamideYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.1 g (10 mmole) of 2-{N-(2-aminoethyl)]aminomethyl-2,3-dihydrobenzodioxin and 1.3 g (10 mmole) of diisopropylethylamine in 100 ml of dichloromethane stored in an ice bath was added 1.8 g (7.2 mmole) (-)-10-camphorsulfonyl chloride. The mixture was allowed to stir overnight at room temperature. The reaction was next washed with saturated aqueous sodium bicarbonate, with saturated sodium chloride, dried over sodium sulfate, filtered and evaporated in vacuum. Column chromatography on 100 g of silica gel with chloroform as eluant, followed by crystallization from isopropanol gave 1.3 g of the title compound, m.p. 149°-152° C.

Workup

  1. washThe reaction was next washed with saturated aqueous sodium bicarbonate, with saturated sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuum
  5. customColumn chromatography on 100 g of silica gel with chloroform as eluant, followed by crystallization from isopropanol

Sources & evidence

ORD record
ord-9fc6c479cab444be8a840ba05844be6d
Source dataset
uspto-grants-1992_06
Patent number
US05126367

Reaction notes

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