Dibutyl sulfoxide → (4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-12-propyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

Participants

Role	Name	HCID	Charge
Reactant	Dibutyl sulfoxide	HCID 16568	—
Reactant	(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol	HCID 73211769	—
Product	(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-12-propyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol	HCID 89984906	—

Reaction Steps

The title compound 5 was synthesized similar to the procedure described in Example 1 for compound 3 using dibutyl sulfoxide instead of DMSO. After column chromatography, 227 mg (86.3% yield, 99.4 purity) of compound 5 was isolated as an off-white solid as a mixture of two epimers in a 95.4:4.6 ratio.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315514B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-7a27baa4a6a845e18358cac6be428235
Source note	uspto-grants-2016_04