Lithium Hydroxide → (1-{2-[2-(2-Oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)acetic acid

HRID 2178538Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([O:24]C)=[O:23])[CH2:17]1.[Li+].[OH-]>CO.O>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:17]1

Participants

Conditions

Temperature: 30 °C

Procedure

Methyl (1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)acetate a13-1 (500 mg, 0.87 mmol, 1 eq) is dissolved in MeOH/H2O (4 ml/1 ml) and LiOH (47 mg, 1.7 mmol, 2 eq) is added. The reaction mixture is stirred at 30° C. for 1 hour, then quenched with HCl 1M (100 μl). The resulting mixture is diluted with n-butanol (15 ml), and stirred overnight at room temperature. After phase separation the organic layer is dried on Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 229 mg of (1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)acetic acid a14-1 as a colorless oil which is used in the next step without any further purification.

Workup

customquenched with HCl 1M (100 μl)
additionThe resulting mixture is diluted with n-butanol (15 ml)
stirringstirred overnight at room temperature
customAfter phase separation the organic layer
customis dried on Na2SO4
filtrationfiltered
concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record: ord-e54fe7e363a3425e93593ad8dcc7b647
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067930B2

Reaction notes

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