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

HRID 1350777Notes

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-88f7ff3fe4dc401bac16a9aa54e4f55f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214802B2

Reaction notes

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