Hydrochloric Acid → (3S,4R)-1-(tert-Butoxycarbonyl)-4-(4-fluorophenyl)piperidine-3-carboxylic acid

HRID 1744687Notes

Reaction equation

[Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]2[C:22]([O:24]CC)=[O:23])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][C@@H:9]([C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=2)[C@H:10]([C:22]([OH:24])=[O:23])[CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 75 °C

Procedure

Excess sodium metal was added to a stirred solution of the product of step E (0.651 g, 1.85 mmol) in methanol (5.0 mL) at ambient temperature, and the resulting solution was heated to 75° C. After approximately 1 h, 5 M sodium hydroxide (3.0 mL) was added and the reaction mixture heated to 100° C. for an additional 1 h. After cooling to room temperature, the reaction mixture was acidified to pH 5 with 2 N hydrochloric acid and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was used without further purification in the subsequent reaction.

Workup

temperaturethe reaction mixture heated to 100° C. for an additional 1 h
temperatureAfter cooling to room temperature
extractionextracted three times with methylene chloride
washThe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe crude product was used without further purification in the subsequent reaction

Sources & evidence

ORD record: ord-3fba6e4a63124ea5be1c1bf6af29e315
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07015235B2

Reaction notes

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