Hydrochloric Acid → 4-{4-[2-(tert-Butyldimethylsilanyloxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

HRID 658231Notes

Reaction equation

HRID 658231 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:8][CH2:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:13][CH:12]=1)=[O:4].Cl>CO>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:23])[CH3:22])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 684912491-(Tert-butyl) 3-methyl 4-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)-5,6-dihydropyridine-1,3(2h)-dicarboxylate

Product 1

HCID 684257344-{4-[2-(tert-Butyldimethylsilanyloxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mg (1.40 g, 58 mmol) was added to a sol. of compound 4-{4-[2-(tert-Butyldimethylsilanyloxy)ethoxy]phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (8.10 g, 17 mmol) in MeOH (40 mL) under Ar. The mixture was stirred for 1 h while maintaining the temperature below 30° C. Aq. 1M HCl (115 mL, 115 mmol) was added dropwise and the mixture was stirred for 1 h. The mixture was extracted with EtOAc (2×). The combined org. layers were washed with water, brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 2:1) yielded a 2:3 trans/cis mixture of the title compound (7.6 g, 93%). LC-MS: tR=1.23 min, ES+=508.47.

Workup

  1. temperaturewhile maintaining the temperature below 30° C
  2. stirringthe mixture was stirred for 1 h
  3. extractionThe mixture was extracted with EtOAc (2×)
  4. washlayers were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (EtOAc/heptane 2:1)
  9. customyielded

Sources & evidence

ORD record
ord-e03646a22e32472babcd6d0a6bef432c
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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