Tetralin → HCID 11769400, compound

HRID 2194980Notes

Reaction equation

C1C2C(=CC=CC=2)CCC1.[CH:11]1([C:21]([OH:23])=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.S(Cl)([Cl:26])=O>>[C@@H:11]1([C:21]([Cl:26])=[O:23])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1

Participants

Reactant 3

HCID 8404Tetralin2×

HCID 24386Thionyl Chloride

HCID 125981461,2,3,4-Tetrahydro-1-naphthoic acid2×

Product 1

HCID 11769400HCID 11769400, compound

Procedure

According to Route A, 1,2,3,4-tetrahydronaphthalene (Compound VI) is converted into 1,2,3,4-tetrahydro-1-naphthoic acid (Compound VII), which is optically resolved to obtain the S-enantiomer (Compound VIIA). The optically enriched acid then is reacted with thionyl chloride to afford (S)-1,2,3,4-tetrahydro-1-naphthoyl chloride (Compound VIIIA). This acid chloride is reacted with Compound III to afford N-(1-azabicyclo[2.2.2]oct-3S-yl)-(1,2,3,4-tetrahydronaphthalen-1S-ylmethyl)amine (Compound IXA), which subsequently is converted to palonosetron hydrochloride over several steps.

Workup

customto obtain the S-enantiomer (Compound VIIA)

Sources & evidence

ORD record: ord-2e7636ced41c4a95a2be3cde7b23f2f2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334388B2

Reaction notes

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