Hydrochloric Acid → 4-((1R,2R)-2-(((3,5-difluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine hydrochloride

HRID 1468863Notes

Reaction equation

HRID 1468863 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([F:31])[C:26]=1[S:27]([CH3:30])(=[O:29])=[O:28])[CH2:5][O:6][CH2:7][C@@H:8]1[CH2:10][C@@H:9]1[CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1.[ClH:32].O1CCOCC1>C(Cl)Cl>[ClH:32].[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([F:31])[C:26]=1[S:27]([CH3:30])(=[O:28])=[O:29])[CH2:5][O:6][CH2:7][C@@H:8]1[CH2:10][C@@H:9]1[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71116058tert-butyl 4-((1R,2R)-2-(((3,5-difluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine-1-carboxylate

Product 1

HCID 867177984-((1R,2R)-2-(((3,5-difluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-((1R,2R)-2-(((3,5-difluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine-1-carboxylate (Step B product, 1.85 g, 4.03 mmol) was dissolved in DCM (20 ml) and HCl in dioxane (4 M solution, 10.60 ml, 40 mmol) was added. The mixture was stirred at RT for 1 h. The solvents were evaporated to afford 1.6 g (100%) of the desired product which was used without further purification. LC/MS (m/z): 360 (M+H)+.

Workup

  1. customThe solvents were evaporated

Sources & evidence

ORD record
ord-9552a27d95d844afaead36108aad6fd9
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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