Hydrochloric Acid → 2-(4-Aminotetrahydro-2H-pyran-4-yl)-1-[(4S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethyl-1-piperidinyl]ethanone

HRID 1888117Notes

Reaction equation

HRID 1888117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:34])[CH2:13][CH2:12][N:11]([C:14](=[O:31])[CH2:15][C:16]3([NH:22]C(=O)C4C=CC=CC=4)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:10][C:9]2([CH3:33])[CH3:32])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:22][C:16]1([CH2:15][C:14]([N:11]2[CH2:12][CH2:13][C@@:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([OH:34])[C:9]([CH3:33])([CH3:32])[CH2:10]2)=[O:31])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59444213HCID 59444213, compound

Product 1

HCID 594442112-(4-Aminotetrahydro-2H-pyran-4-yl)-1-[(4S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethyl-1-piperidinyl]ethanoneYield 101.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To (S)-tert-butyl 4-(2-(4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-2-oxoethyl)tetrahydro-2H-pyran-4-ylcarbamate (from step 3, 0.17 g, 0.35 mmol) was added 4.0N HCl in dioxane (2 mL) at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 24 h. At the conclusion of this period, the reaction mixture was concentrated under reduced pressure and then partitioned between ethyl acetate (20 mL) and 1N NaOH (10 mL). The ethyl acetate layer was separated, washed with brine (20 mL), dried over sodium sulfate and concentrated under reduced pressure to yield the title compound (0.135 g) as a foamy solid. MS (ESI+)=381.1 (M+H)+.

Workup

  1. additionUpon completion of addition
  2. concentrationAt the conclusion of this period, the reaction mixture was concentrated under reduced pressure
  3. custompartitioned between ethyl acetate (20 mL) and 1N NaOH (10 mL)
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b4101661e4b48698f2578933be6f4f6
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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