CAS 3886-70-2

(R)-1-(naphthalen-1-yl)ethan-1-amine

Codes: EVOCA-003, CINA-006

Application context (from source-drug indications)

Secondary hyperparathyroidismEvocalcetParathyroid carcinomaEvocalcetPrimary hyperparathyroidismEvocalcetHyperparathyroidismEvocalcetHypercalcaemiaCinacalcet HydrochlorideSecondary hyperparathyroidismCinacalcet HydrochlorideHyperparathyroidismCinacalcet HydrochloridePrimary hyperparathyroidismCinacalcet HydrochlorideChronic renal impairmentCinacalcet HydrochlorideCardiogenic oedemaCinacalcet Hydrochloride

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
Evocalcet	Tier C — Watch / trade	-
Cinacalcet Hydrochloride	Tier B — Position early	-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

EvocalcetOriginator routesteps: 6total yield: 12.77 g

(R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate→tert-butyl (R)-3-(((2-nitrophenyl)sulfonyl)oxy)pyrrolidine-1-carboxylate→(R)-1-(naphthalen-1-yl)ethan-1-amine→tert-butyl (S)-3-(((R)-1-(naphthalen-1-yl)ethyl)amino)pyrrolidine-1-carboxylate→propan-2-ol compound with (S)-N-((R)-1-(naphthalen-1-yl)ethyl)pyrrolidin-3-amine (1:1) hydrochloride→(S)-N-((R)-1-(naphthalen-1-yl)ethyl)pyrrolidin-3-amine→ethyl 2-(4-bromophenyl)acetate→ethyl 2-(4-((S)-3-(((R)-1-(naphthalen-1-yl)ethyl)amino)pyrrolidin-1-yl)phenyl)acetate hydrochloride→2-(4-((S)-3-(((R)-1-(naphthalen-1-yl)ethyl)amino)pyrrolidin-1-yl)phenyl)acetic acid

Cinacalcet HydrochlorideOriginator routesteps: 5total yield: 29.2 kg

1-bromo-3-(trifluoromethyl)benzene→prop-2-yn-1-ol→3-(3-(trifluoromethyl)phenyl)prop-2-yn-1-ol→3-(3-(trifluoromethyl)phenyl)propan-1-ol→3-(3-(trifluoromethyl)phenyl)propanal→(R)-1-(naphthalen-1-yl)ethan-1-amine

Cinacalcet HydrochlorideOptimised routesteps: 5total yield: /

1-bromo-3-(trifluoromethyl)benzene→3-(3-(trifluoromethyl)phenyl)propan-1-ol→(R)-1-(naphthalen-1-yl)ethan-1-amine→ethyl acrylate→ethyl (E)-3-(3-(trifluoromethyl)phenyl)acrylate→(E)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-ol→1-(3-chloropropyl)-3-(trifluoromethyl)benzene

Cinacalcet HydrochlorideOptimised routesteps: 4total yield: 25.8 g

(R)-1-(naphthalen-1-yl)ethan-1-amine→3-(trifluoromethyl)benzaldehyde→acetic anhydride→(E)-3-(3-(trifluoromethyl)phenyl)acrylic acid→3-(3-(trifluoromethyl)phenyl)propanoic acid→(R)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide

Cinacalcet HydrochlorideProcess routesteps: 5total yield: 371 g

(R)-1-(naphthalen-1-yl)ethan-1-amine→3-(3-(trifluoromethyl)phenyl)propanoic acid→(R)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide→3-(trifluoromethyl)aniline→acrylonitrile→2-chloro-3-(3-(trifluoromethyl)phenyl)propanenitrile→2-chloro-3-(3-(trifluoromethyl)phenyl)propanoic acid

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