Triethylamine → HCID 53720630, compound

HRID 979160Notes

Reaction equation

HRID 979160 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[C@@H:15]([CH2:16][OH:17])[CH2:14][N:13]([CH3:18])[CH2:12][C@H:11]3[C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl.CO>[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[C@@H:15]([CH2:16][O:17][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:14][N:13]([CH3:18])[CH2:12][C@H:11]3[C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13851321HCID 13851321, compound

Product 1

HCID 53720630HCID 53720630, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.69 g of (±)-[4R*,4aS*,10bR*]-7-bromo-4-(hydroxymethyl)-1,3,4,4a,5,10b-hexahydro-9-methoxy-2-methyl-2 H-[1]benzopyrano[4,3-c]pyridine and 0.82 ml triethylamine in 60 ml CH2Cl2 is added 0.42 ml of methanesulfonyl chloride. After 15 min. 1 drop methanol is added and the reaction mixture is washed with saturated NaHCO3 and dried over Na2SO4. Filtration and removal of solvents under reduced pressure yields (±)-[4R*,4aS*,10bR*]-7-bromo-4-(methylsulfonyloxymethyl)-1,3,4,4a,5,10b-hexahydro-9-methoxy-2-methyl-2H-[1]benzopyrano[4,3-c]pyridine.

Workup

  1. washthe reaction mixture is washed with saturated NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and removal of solvents under reduced pressure

Sources & evidence

ORD record
ord-b597c97a938549e0929c0b15adb914b0
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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