3-Fluorobenzaldehyde → HCID 16039596, compound

HRID 252070Notes

Reaction equation

HRID 252070 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:13][C:12]3[C:7](=[C:8]([CH3:21])[CH:9]=[C:10]([CH2:14][CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[CH:11]=3)[C:6]2=[O:22])[CH2:3][CH2:2]1.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[CH:1]1([CH2:4][N:5]2[CH2:13][C:12]3[C:7](=[C:8]([CH3:21])[CH:9]=[C:10]([CH2:14][CH:15]4[CH2:20][CH2:19][N:18]([CH2:27][C:26]5[CH:29]=[CH:30][CH:31]=[C:24]([F:23])[CH:25]=5)[CH2:17][CH2:16]4)[CH:11]=3)[C:6]2=[O:22])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 680093-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 57672258HCID 57672258, compound

Product 1

HCID 16039596HCID 16039596, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-Cyclopropylmethyl-7-methyl-5-piperidin-4-ylmethyl-2,3-dihydro-isoindol-1-one (30 mg, 0.110 mmol) in methanol (2 mL) was slowly added acetic acid (1 mL). After stirring at room temperature for 5 minutes, 3-Fluoro-benzaldehyde (12.8 μL, 0.121 mmol) and sodium cyanoborohydride (8 μL, 0.111 mmol) were added dropwisely. The mixture stirred at room temperature for 2 hours and was neutralized with saturated sodium bicarbonate (10 mL). The aqueous mixture was extracted with dichloromethane and the organics were dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (10-40% ethyl acetate in hexanes) provided the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.70-7.23 (m, 1H), 7.09-7.03 (m, 3H), 6.97-6.92 (m, 2H), 4.41 (s, 2H), 3.48-3.44 (m, 4H), 2.88-2.85 (d, 2H), 2.71 (s, 3M), 2.60-2.57 (d, 2H), 1.93 (t, 2H), 1.64-1.50 (m, 3H), 1.36-1.28 (m, 2H), 1.04 (m, 1H), 0.60-0.55 (m, 2H), 0.34-0.32 (m, 2H)

Workup

  1. stirringThe mixture stirred at room temperature for 2 hours
  2. extractionThe aqueous mixture was extracted with dichloromethane
  3. dry with materialthe organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2b93db4ec0ee479a93b861dc49ca5144
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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