Bromomethylcyclopropane → HCID 70586393, compound

HRID 904217Notes

Reaction equation

HRID 904217 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@H:9]3[NH:20][CH2:19][CH2:18][C@@:15]4([C:16]=2[CH:17]=1)[C@H:10]3[CH2:11][CH2:12][C:13](=[O:21])[CH2:14]4.[CH:22]1([CH2:25]Br)[CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO>[ClH:1].[CH:22]1([CH2:25][N:20]2[CH2:19][CH2:18][C@@:15]34[C:16]5[CH:17]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=5[CH2:8][C@@H:9]2[C@@H:10]3[CH2:11][CH2:12][C:13](=[O:21])[CH2:14]4)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 70585373HCID 70585373, compound

Product 1

HCID 70586393HCID 70586393, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A sample of 3-methoxymorphinan-6-one hydrochloride (3.08 g, 10 mmol, prepared in Part IC), was reacted with cyclopropylmethyl bromide in the presence of sodium bicarbonate as described in Example 1D. After chromatography on Silica Gel G using 20:1 V/V chloroform-methanol, 2.5 g of the desired product was isolated as a syrup. This was converted to the hydrochoride salt to yield 2.1 g (58%) of TR-5152, mp 265°-267° C.

Sources & evidence

ORD record
ord-8f20794ae9c7456fa53222f4314e5227
Source dataset
uspto-grants-1980_10
Patent number
US04230712

Reaction notes

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