Hydrochloric Acid → (6-Chloro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride

HRID 222413Notes

Reaction equation

HRID 222413 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=C(Cl)C=CC=2N=1>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:9][CH2:10][C@@H:11]3[CH2:15][CH2:14][NH:13][CH2:12]3)[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 771752,6-DichlorobenzoxazoleHCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 59178006(6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 131728778(6-Chloro-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 2,6-dichloro-benzooxazole (commercially available) and subsequent cleavage of the tert-butyloxy carbonyl-protecting group through treatment with HCl in dioxane. MS (m/e): 252.2 (MH+).

Sources & evidence

ORD record
ord-9d0366cd428f464a9f92da35da2bfa66
Source dataset
uspto-grants-2012_06
Patent number
US08207220B2

Reaction notes

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