Hydrochloric Acid → Tert-butyl 3-(1(r,s)-carboxyethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176207Notes

Reaction equation

HRID 1176207 reaction equation
C([O:3][C:4]([CH:6]([O:8][CH:9]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[CH:17][CH:16]=2)[CH2:13][CH2:12][N:11]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:10]1)[CH3:7])=[O:5])C.Cl>CO.[OH-].[Na+]>[C:4]([CH:6]([O:8][CH:9]1[CH:14]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[CH:19][CH:20]=2)[CH2:13][CH2:12][N:11]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH2:10]1)[CH3:7])([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68501234Tert-butyl 3-(1(r,s)-ethoxycarbonylethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]-phenyl}piperidine-1-carboxylate

Product 1

HCID 68497738Tert-butyl 3-(1(r,s)-carboxyethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.33 g of tert-butyl 3-(1(R,S)-ethoxycarbonylethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 4 ml of methanol and 1 ml of 2N NaOH is stirred at room temperature over 18 hours. The reaction mixture is admixed with 1.5 ml of 4N HCl and extracted with EtOAc. The organic phase is washed with brine, dried over sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a yellowish oil from the residue. Rt=5.33.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-371f41d5665549068141a09a5a051eaa
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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