o-Fluorobenzaldehyde → HCID 89650060, compound

HRID 1479049Notes

Reaction equation

C(O[K])(C)(C)C.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]([C:21]([F:24])([F:23])[F:22])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].F[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>O1CCOCC1.O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([O:20][C:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=[O:29])[CH:16]([C:21]([F:24])([F:22])[F:23])[CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

tBuOK (136 mg; 1.21 mmol; 1.5 eq.) was added to a solution of 4-hydroxy-3-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester (239 mg; 0.89 mmol; 1.1 eq.) in 1,4-dioxane (10 mL) and the reaction mixture was stirred at 50° C. for 15 minutes. After cooling down to room temperature, 2-fluoro-benzaldehyde (100 mg; 0.81 mmol; 1 eq.) was added and the reaction was stirred at 50° C. for 30 minutes. The solution was diluted with water and extracted with EA (3×). The combined organics were dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (10% to 30% EA in heptane) afforded the title compound (181 mg, 60%) as colourless oil. HPLC (max plot) 99.9%, Rt 5.02 min. UPLC/MS: (MS+) 274.2 ([M-(Boc)+H]+).

Workup

temperatureAfter cooling down to room temperature
stirringthe reaction was stirred at 50° C. for 30 minutes
extractionextracted with EA (3×)
dry with materialThe combined organics were dried over magnesium sulfate
concentrationconcentrated in vacuo
customPurification by column chromatography (10% to 30% EA in heptane)

Sources & evidence

ORD record: ord-cfac339751c14500a20e54900e53de7a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403835B2

Reaction notes

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