(R)-Methyl 4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)benzoate → (R)-4-((3-(Dimethylamino)pyrrolidin-1-yl)methyl)benzoic acid

HRID 1907692Notes

Reaction equation

HRID 1907692 reaction equation
[CH3:1][N:2]([CH3:19])[C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH2:4]1>Cl>[CH3:1][N:2]([CH3:19])[C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH2:4]1

Participants

3

Reactant 1

HCID 59737485(R)-Methyl 4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)benzoate

Product 1

HCID 59737509(R)-4-((3-(Dimethylamino)pyrrolidin-1-yl)methyl)benzoic acidYield 124.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
-78 °C

Procedure

Compound 6 (0.55 g, 2.1 mmol) was heated to 110° C. in 2N aqueous hydrochloric acid (7 mL) for 18 h then cooled to −78° C. and lyophilized to give compound 7 as a grey solid (0.65 g, 97% yield). LRMS: 248.2 (calc), 249.0 (obs).

Sources & evidence

ORD record
ord-bf332639587849eebc950eb7b01f5929
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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