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

HRID 1969749Notes

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>Cl.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

Conditions

Temperature: 60 °C

Procedure

Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate (3.65 g, 10.38 mmol) was dissolved in a mixture of HCl (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 concd 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)+.

Workup

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

Sources & evidence

ORD record: ord-afa26b44ac9740c7b73aac6c03b6b679
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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