Triethylamine → 7,7-Dimethyl-9-oxononyl methanesulfonate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanesulfonyl chloride	HCID 31297	—
Reactant	(E)-9-methoxy-7,7-dimethylnon-8-en-1-ol	HCID 57989140	—
Reactant	(R)-4-Hydroxy-7-(1-hydroxy-2-(9-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3,3-dimethylnonylamino)ethyl)benzo[d]thiazol-2(3H)-one formate	HCID 67292868	—
Solvent	Dichloromethane	HCID 6344	—
Product	7,7-Dimethyl-9-oxononyl methanesulfonate	HCID 57988922	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A mixture of (E)-9-methoxy-7,7-dimethylnon-8-en-1-ol and (Z)-9-methoxy-7,7-dimethylnon-8-en-1-ol (example 279, step d) (1.6 g) was dissolved in dichloromethane (15 mL) and triethylamine (1.33 mL) was added then the mixture was cooled to 0° C. in an ice bath under argon. Methanesulfonyl chloride (0.68 mL) was added dropwise over 5 minutes and the reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for 1 hour. The reaction mixture was washed with brine (2×30 mL), dried over magnesium sulfate, filtered and evaporated under vacuum to give the crude product. Purification was by silica gel chromatography, eluting with 0-100% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless oil. Yield 1.2 g.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08148373B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-ad25a36aeb614c708958eb31f549312f
Source note	uspto-grants-2012_04