Sodium Bicarbonate → methyl 2-((R)-(5-chloro-2-methylphenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate

HRID 218447Notes

Reaction equation

HRID 218447 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:30])=[C:6]([C@H:8]([O:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH3:29])=[O:27])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:7]=1.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:30])=[C:6]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[O:28][CH3:29])[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58011516(R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 58011553methyl 2-((R)-(5-chloro-2-methylphenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamateYield 100.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(R)-tert-Butyl 3-((R)-(5-chloro-2-methylphenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (1.0 g, 2.27 mmol) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (20 mL). The reaction mixture was stirred at room temperature for 2 h, TLC showed the starting material disappeared, a solution of saturated sodium bicarbonate was added dropwise to adjust pH=7-8. The resulting mixture was extracted with CH2Cl2 (3×30 mL), washed with brine, dried over Na2SO4, concentrated in vacuo to afford methyl 2-((R)-(5-chloro-2-methylphenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate (780 mg, 100%).

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2 (3×30 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-363d269d774a47db90efb7061747c395
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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