Methanol → HCID 86753311, compound

HRID 355752Notes

Reaction equation

HRID 355752 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@@H:10]([N:24]([O:36][CH3:37])[C:25](=[O:35])[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=3)[CH2:9][CH2:8][C@@:7]4([OH:38])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.[CH3:39][Si](C=[N+]=[N-])(C)C.C(N(C(C)C)CC)(C)C.CO>C(#N)C>[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@@H:10]([N:24]([O:36][CH3:37])[C:25](=[O:35])[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=3)[CH2:9][CH2:8][C@@:7]4([OH:38])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][CH3:39])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 86753312HCID 86753312, compound

Product 1

HCID 86753311HCID 86753311, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(N-methoxy-3,4-dichlorophenylacetamido)morphinan (197 mg, 0.35 mmol), trimethylsilyldiazomethane (10% solution in CH2Cl2, 0.57 g, 0.5 mmol), diisopropylethylamine (65 mg, 0.5 mmol), methanol (0.2 ml), and acetonitrile (2 ml) was stirred at room temperature for 13 h. After evaporation of the solvent, the residual oil was purified by preparative thin layer chromatography (1 mm thick plate, CH2Cl2 /MeOH: 10/1) to give 47 mg of amorphous solid. This was purified again by preparative thin layer chromatography (1 mm thick plate, CH2Cl2 /MeOH: 10/1) to give 25 mg of amorphous solid as desired product.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residual oil was purified by preparative thin layer chromatography (1 mm thick plate, CH2Cl2 /MeOH: 10/1)

Sources & evidence

ORD record
ord-78d674f32e24418bba7339b86ba6f044
Source dataset
uspto-grants-1998_11
Patent number
US05834478

Reaction notes

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