(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride → HCID 66874301, compound

HRID 249838Notes

Reaction equation

HRID 249838 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[O:15][C:16]3[C:17](=[C:19]([C:23](O)=[O:24])[CH:20]=[CH:21][CH:22]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:28][C@H:29]1[CH:34]2[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]2)[CH2:30]1>>[N:31]12[CH2:30][CH:29]([NH:28][C:23]([C:19]3[C:17]4[N:18]=[C:14]([N:11]5[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12]5)[O:15][C:16]=4[CH:22]=[CH:21][CH:20]=3)=[O:24])[CH:34]([CH2:35][CH2:36]1)[CH2:33][CH2:32]2

Participants

3

Reactant 2

HCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 66873553HCID 66873553, compound

Product 1

HCID 66874301HCID 66874301, compound

Procedure

Following general procedure GP-C1, A mixture of 2-[4-(tert-butoxycarbonyl)piperazin-1-yl]benzoxazole-4-carboxylic acid and (S)-(−)-3-aminoquinuclidine dihydrochloride were coupled to provide tert-butyl 4-[4-(quinuclidine-8-ylcarbamoyl]benzoxazol-2-yl)piperazine-1-carboxylate (85 mg, 0.19 mmol) to which was added TFA (0.17 mL, 2.3 mmol). The reaction mixture was stirred at room temperature for 12 h, and then concentrated under reduced pressure. The TFA salt was converted to the dihydrochloride salt following general procedure GP-D1. 1H NMR and MS consistent.

Sources & evidence

ORD record
ord-7b877cfc6d3245c8a47164c5e2b55d6b
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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