Hydrochloric Acid → (7-Fluoro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride

HRID 403333Notes

Reaction equation

HRID 403333 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:9][CH2:10][CH:11]3[CH2:15][CH2:14][NH:13][CH2:12]3)[O:8][C:4]=2[CH:3]=1.Cl.C(OC(N1CC[C@@H](CN)C1)=O)(C)(C)C.ClC1OC2C([F:43])=CC=CC=2N=1>O1CCOCC1>[ClH:1].[F:43][C:3]1[C:4]2[O:8][C:7]([NH:9][CH2:10][C@@H:11]3[CH2:15][CH2:14][NH:13][CH2:12]3)=[N:6][C:5]=2[CH:16]=[CH:17][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 154287392-Chloro-7-fluoro-1,3-benzoxazoleHCID 59178006(6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 131728780(7-Fluoro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described for the synthesis of (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-ylmethyl-amine; hydrochloride (example 1, step 2) the title compound was prepared from (S)-3-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester and 2-chloro-7-fluoro-benzooxazole (Bioorganic & Medicinal Chemistry Letters 2007, 17, 4689) and subsequent cleavage of the tert-butyloxy carbonyl-protecting group through treatment with HCl in dioxane. MS (m/e): 236.1 (MH+).

Sources & evidence

ORD record
ord-b4190d2963264336bbf9cc9378b06f62
Source dataset
uspto-grants-2014_06
Patent number
US08748430B2

Reaction notes

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