Hydrochloric Acid → cis-1-{2-[(3Rs,5rs)-3-(aminomethyl)-5-hydroxy-1-piperidinyl]ethyl}-7-fluoro-2(1h)-quinolinone-hydrochloride

HRID 657137Notes

Reaction equation

HRID 657137 reaction equation
CC([Si](C)(C)[O:6][C@H:7]1[CH2:12][N:11]([CH2:13][CH2:14][N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=3)[CH:18]=[CH:17][C:16]2=[O:26])[CH2:10][C@@H:9]([CH2:27][NH:28]C(=O)OC(C)(C)C)[CH2:8]1)(C)C.[ClH:38].O1CCOCC1>C(Cl)Cl.CO>[ClH:38].[NH2:28][CH2:27][C@H:9]1[CH2:8][C@@H:7]([OH:6])[CH2:12][N:11]([CH2:13][CH2:14][N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=3)[CH:18]=[CH:17][C:16]2=[O:26])[CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131729314cis-1,1-Dimethylethyl ({(3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-[2-(7-fluoro-2-oxo-1 (2h)-quinolinyl)ethyl]-3-piperidinyl}methyl)carbamate

Product 1

HCID 68992139cis-1-{2-[(3Rs,5rs)-3-(aminomethyl)-5-hydroxy-1-piperidinyl]ethyl}-7-fluoro-2(1h)-quinolinone-hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To cis-1,I-dimethylethyl ({(3RS,5RS)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-3-piperidinyl}methyl)carbamate (410 mg; 0.78 mmol) in DCM (9 ml) and MeOH (1 ml) was added 4N HCl in 1,4-dioxane (1 ml; 4.0 mmol) and the reaction was allowed to stir at room temperature under nitrogen for 2 hours. The reaction was concentrated under reduced pressure to give the desired compound (270 mg; 100%) as a yellow solid which was used in the next reaction without further purification.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6682dd949264872aedb0eb44ccc65fd
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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