1,1'-Sulfinylbis(propane) → (4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-12-ethyl-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

Participants

Role	Name	HCID	Charge
Reactant	1,1'-Sulfinylbis(propane)	HCID 20252	—
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-12-ethyl-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 86711660	—

Reaction Steps

The title compound 4 was prepared similar to the procedure described in Example 1 for compound 3 using dipropyl sulfoxide instead of DMSO. After column chromatography, 117 mg (53.7% yield, >99.9 purity) of compound 4 was isolated as an off-white solid as a mixture of two epimers in a 96.1:3.9 ratio.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315514B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-ff00daddab954ff6a671d18271758808
Source note	uspto-grants-2016_04