Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate → 4-(Dibenzylamino)-2-methylcyclopentanecarboxylic acid

HRID 1969638Notes

Reaction equation

HRID 1969638 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:9]1[CH2:13][CH:12]([C:14]([O:16]CC)=[O:15])[CH:11]([CH3:19])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]1[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH:11]([CH3:19])[CH2:10]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 58010318Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate

Product 1

HCID 585575354-(Dibenzylamino)-2-methylcyclopentanecarboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate (3.65 g, 10.38 mmol) was dissolved in a mixture of HC; (6 N aqueous, 20 mL) and 1,4-dioxane (50 mL) and the resulting mixture was heated at about 60° C. for about 72 h. The organic solvent was removed under reduced pressure. The aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 (40 mL) and extracted with EtOAc (50 mL). The organic phase was washed with brine (40 mL), dried over anhydrous MgSO4 and coned under reduced pressure to yield 4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid (3.3 g, 98%) as a white amorphous solid: LC/MS (Table 1, Method a) Rt=1.66 min.; MS m/z 324 (M+H)+. The procedure in Step A, Preparation #33 was utilized to provide (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. additionThe aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 (40 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic phase was washed with brine (40 mL)
  5. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-c6e497233efa4ecc9aa642349d79a46a
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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