4-Fluorobenzaldehyde → HCID 58531569, compound

HRID 1889624Notes

Reaction equation

HRID 1889624 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:17]=1)[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.[Na]>C(Cl)Cl.CC(O)C>[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:15]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:17]=2)[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 5360545SodiumHCID 66616563HCID 66616563, compound

Product 1

HCID 58531569HCID 58531569, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(aminomethyl)-5-(4-fluorophenoxy)benzylcarbamate (1.37 g, 3.96 mmol) in CH2Cl2 (15 mL) and 2-propanol (15 mL) was added 4-fluorobenzaldehyde (0.42 mL, 3.96 mmol). The reaction mixture was stirred at rt. under nitrogen for 40 min, and then treated with sodium triacetoxyhydroborate (1.76 g, 8.31 mmol). The resulting mixture was stirred at rt for 2 h. The reaction mixture was concentrated and the residue was partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer (clear solution) was washed with brine and dried over MgSO4. The filtrate was concentrated. The sample was purified by flash chromatography. Elution with 0-35% of ethyl acetate in CH2Cl2 gave the product as viscous oil (1.2 g, 67%). 1H NMR (CD3OD): δ 7.35-7.32 (m, 2H), 7.13-6.99 (m, 7H), 6.87 (s, 1H), 6.80 (s, 1H), 4.20 (s, 2H), 3.70 (s, 2H), 1.44 (s, 9H); MS (ESI): (M−H)−=513.1.

Workup

  1. stirringThe resulting mixture was stirred at rt for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between saturated NaHCO3 solution and ethyl acetate
  4. washThe organic layer (clear solution) was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe filtrate was concentrated
  7. customThe sample was purified by flash chromatography
  8. washElution with 0-35% of ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-3d16af249aae4ced8e89dba8aabb947c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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