1,4-Dioxane → ((+/-)-(cis)-2-Aminocyclobutyl)((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)methanone hydrochloride

HRID 42552Notes

Reaction equation

HRID 42552 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]([C@H:16]3[CH2:19][CH2:18][C@H:17]3[NH:20]C(=O)OC(C)(C)C)=[O:15])[CH2:10][C:9]2([CH3:29])[CH3:28])=[CH:4][CH:3]=1.O1CCOCC1>Cl>[ClH:1].[NH2:20][C@H:17]1[CH2:18][CH2:19][C@H:16]1[C:14]([N:11]1[CH2:12][CH2:13][C@@:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:30])[C:9]([CH3:29])([CH3:28])[CH2:10]1)=[O:15]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 59475009HCID 59475009, compound

Product 1

HCID 68493990((+/-)-(cis)-2-Aminocyclobutyl)((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl (±)-(cis)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carbonyl)cyclobutylcarbamate (160 mg, 0.366 mmol) in 4 M HCl in dioxane (5 mL, 20.00 mmol HCl) was stirred at room temperature for 3 hours. After this time, the mixture was concentrated in vacuo, then concentrated 3× from methylene chloride to remove residual HCl and dioxane, to yield the title compound as a colorless solid which was used without purification in the next step. MS (ESI+)=327.3 (M+H)+.

Workup

  1. concentrationAfter this time, the mixture was concentrated in vacuo
  2. concentrationconcentrated 3× from methylene chloride
  3. customto remove residual HCl and dioxane

Sources & evidence

ORD record
ord-973170c6a917419ea1041d25ce50b96a
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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