Hydrochloric Acid → (2R)-2-amino-1-(4-(4-chloro-3-methoxyphenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride

HRID 1820209Notes

Reaction equation

HRID 1820209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:30])[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C@H:15]([NH:19]C(=O)OC(C)(C)C)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:29])[CH3:28])=[CH:4][C:3]=1[O:31][CH3:32].Cl>O1CCOCC1>[ClH:1].[NH2:19][C@H:15]([CH:16]([CH3:18])[CH3:17])[C:14]([N:11]1[CH2:12][CH2:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:31][CH3:32])[CH:4]=2)([OH:30])[C:9]([CH3:28])([CH3:29])[CH2:10]1)=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57889049tert-butyl (2R)-1-(4-(4-chloro-3-methoxyphenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Product 1

HCID 67299413(2R)-2-amino-1-(4-(4-chloro-3-methoxyphenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (2R)-1-(4-(4-chloro-3-methoxyphenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (153 mg, 0.33 mmol) was added 4N HCl in dioxane (2 mL) and stirred for 60 min. The solvents were removed in vacuo and the resulting solids were dried azeotropically with toluene and then further dried under high vacuum to afford (2R)-2-amino-1-(4-(4-chloro-3-methoxyphenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride as a white solid.

Workup

  1. customThe solvents were removed in vacuo
  2. dry with materialthe resulting solids were dried azeotropically with toluene
  3. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-e4b22b8b45c542bd831803c50d893fac
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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