HCID 10860472, compound → HCID 15382172, compound

HRID 1858345Notes

Reaction equation

HRID 1858345 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][O:23][CH3:24])[CH:4]=[CH:5]2.[Cl-].[C:26]([O:34][CH3:35])(=[O:33])[CH2:27][CH2:28][CH2:29][C:30]([O-])=[O:31]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C:26]([O:34][CH3:35])=[O:33])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][O:23][CH3:24])[CH:4]=[CH:5]2

Participants

5

Reactant 2

HCID 10860472HCID 10860472, compoundHCID 22126164HCID 22126164, compound

Product 1

HCID 15382172HCID 15382172, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4,5α-Epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (2.0 g, 6.1 mmol) and 4-dimethylaminopyridine (0.8 g, 6.5 mmol) were dissolved in absolute CH2Cl2 (20 ml) and methyl glutarate chloride (1.0 g, 6.08 mmol) were added dropwise whilst cooling with ice and the mixture was stirred for 2 hours at this temperature. The reaction mixture was poured onto water (50 ml), the organic phase was washed twice more with 30 ml of water and dried over MgSO4. The solvent was evaporated off and the residue was separated off by flash chromatography (CH2Cl2 /MeOH 9/1).

Workup

  1. temperaturewhilst cooling with ice
  2. additionThe reaction mixture was poured onto water (50 ml)
  3. washthe organic phase was washed twice more with 30 ml of water
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated off
  6. customthe residue was separated off by flash chromatography (CH2Cl2 /MeOH 9/1)

Sources & evidence

ORD record
ord-2cdad9a200b249e58f8c32d58b05c4a4
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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