Sodium Hydroxide → N-Boc-4-(4-carboxy-2-cyclopropyl-2H-pyrazol-3-yl)-piperidine

HRID 2109282Notes

Reaction equation

[OH-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[N:17]([CH:26]3[CH2:28][CH2:27]3)[N:18]=[CH:19][C:20]=2[C:21]([O:23]CC)=[O:22])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>CCO>[C:3]([N:10]1[CH2:11][CH2:12][CH:13]([C:16]2[N:17]([CH:26]3[CH2:28][CH2:27]3)[N:18]=[CH:19][C:20]=2[C:21]([OH:23])=[O:22])[CH2:14][CH2:15]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1.71 mL (3.42 mmol) of 2M NaOH was added to 0.540 g (1.49 mmol) N-Boc-4-(2-cyclopropyl-4-ethoxycarbonyl-2H-pyrazol-3-yl)-piperidine in 15 mL of EtOH. After stirring at 60° C. for 18 h, the solution was concentrated and dissolved in 100 mL of EtOAc (100 mL) and 10 mL of 5% HCl (10 mL). The extract was washed with 50 mL of brine (50 mL), dried over MgSO4, filtered, concentrated, and chromatographed (0-100% EtOAc in hexanes) to give 330 mg of N-Boc-4-(4-carboxy-2-cyclopropyl-2H-pyrazol-3-yl)-piperidine as a white powder.

Workup

concentrationthe solution was concentrated
dissolutiondissolved in 100 mL of EtOAc (100 mL)
washThe extract was washed with 50 mL of brine (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customchromatographed (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-fb4e95eb7d92441e817ea61c165b8b19
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514458B2

Reaction notes

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