(5a,6a)-17-(Cyclopropylmethyl)-4,5-epoxy-6-(methylamino)-morphinan-3,14-diol → 17-cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7beta-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	(5a,6a)-17-(Cyclopropylmethyl)-4,5-epoxy-6-(methylamino)-morphinan-3,14-diol	HCID 15908858	—
Reactant	3-Trifluoromethoxycinnamoyl chloride	HCID 53895214	—
Reactant	17-Cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7beta-methylaminomorphinan	HCID 70220768	—
Reactant	17-Cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7alpha-methylaminomorphinan	HCID 70221550	—
Product	17-cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7alpha-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride	HCID 86756298	68%
Product	17-cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7beta-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride	HCID 86756300	71%

Reaction Steps

The procedure of Example 11 was repeated, except that 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7α-methylaminomorphinan and 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7β-methylaminomorphinan were used instead of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6α-methylaminomorphinan 4 and 3-trifluoromethoxycinnamoyl chloride was used instead of 3,4-dichlorophenylacetyl chloride, thereby preparing 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7α-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride 243 (yield: 68%) and 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7β-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride 244 (yield: 71%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06177438B1
Source dataset	uspto-grants-2001_01
ORD ID	ord-5275fd381aab44369151df181e0a223d
Source note	uspto-grants-2001_01