Water → 2-[(1-Ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-3,3,3-trifluoro-1,2-propanediol

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Sulfite	HCID 24437	—
Reactant	1,4-Bis(dihydroquinidine)phthalazine	HCID 11217202	—
Reactant	1-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene	HCID 11601435	—
Reactant	1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine	HCID 51003674	—
Solvent	tert-Butanol	HCID 6386	—
Product	2-[(1-Ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-3,3,3-trifluoro-1,2-propanediol	HCID 24749152	—

Reaction Conditions

Temperature	30 °C

Reaction Steps

1-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene (Intermediate 12) (100 mg, 0.373 mmole), AD-MIX-α (300 mg) and AD-MIX-β (300 mg) in t-butanol (2 ml) and water (2 ml) were stirred at room temperature. After 1 hour further AD-MIX-α (600 mg) and AD-MIX-β (600 mg) were added and the mixture was heated to 30° C. for 18 h. Sodium sulphite (2 g) was added together with water (5 ml) then stirred for 10 min. Extraction of the mixture with ethyl acetate (3×20 ml) followed by washing of the extract with 2M HCl (x2), 2M NaOH and evaporation of volatiles in vacuo gave a crude product. After purification (silica SPE, 85:15 cyclohexane:ethyl acetate) the title compound was obtained (30 mg, 27%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07902224B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-35d8bc4e2faa4608bc1aefd9ef7eebee
Source note	uspto-grants-2011_03