Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(spiro[1h-indene-1,4'-piperidin]-1'-yl)-2-propanol ethanedioate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Oxalic Acid	HCID 971	—
Reactant	Spiro[indene-1,4'-piperidine]	HCID 10330052	—
Reactant	(2s)-Glycidyl indol-4-yl ether	HCID 10943254	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(2s)-(-)-1-(4-Indolyloxy)-3-(spiro[1h-indene-1,4'-piperidin]-1'-yl)-2-propanol ethanedioate	HCID 131719706	—

Reaction Steps

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and spiro[1H-indene-1,4′-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 80% overall yield. mp 119-120°. FDMS m/e=374 (M+ of free base). α[D]589=−5.51 (c=0.47, methanol).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06172073B2
Source dataset	uspto-grants-2001_01
ORD ID	ord-4332c8484c4b4a5681b194c72e23d094
Source note	uspto-grants-2001_01