Hydrochloric Acid → HCID 66616701, compound

HRID 1889628Notes

Reaction equation

HRID 1889628 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].CO.[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>>[F:20][C:21]([F:30])([F:31])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=2)[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[CH:24][CH:23]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 679964-(Trifluoromethyl)benzaldehydeHCID 2756043tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66616701HCID 66616701, compoundYield 47.9%

Procedure

To a solution of tert-butyl 3-(aminomethyl)benzylcarbamate (0.80 g, 3.39 mmol) in methanol (0.11 g, 3.39 mmol) was added 4-(trifluoromethyl)benzaldehyde (0.45 mL, 3.39 mmol) under nitrogen. The reaction mixture was stirred for 10 min, followed by the addition of sodium triacetoxyborohydride (1.08 g, 5.08 mmol). The resulting mixture was stirred at rt. for 20 h. To the reaction mixture was added 1 N HCl solution and the mixture was concentrated. The residue was extracted with ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over MgSO4, and concentrated to give an oil. The sample was purified by silica gel flash chromatography. Elution with dichloromethane to 30% of ethyl acetate in dichloromethane gave a colorless oil (0.64 g, 47%). 1H NMR (CDCl3): δ 7.61 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.0 Hz, 2H), 7.33-7.22 (m, 4H), 4.34 (m, 2H), 3.89 (s, 2H), 3.82 (s, 2H), 1.48 (s, 9H); MS (ESI): (M+H)+=395.4.

Workup

  1. stirringThe resulting mixture was stirred at rt
  2. waitfor 20 h
  3. concentrationthe mixture was concentrated
  4. extractionThe residue was extracted with ethyl acetate and saturated sodium bicarbonate solution
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe sample was purified by silica gel flash chromatography
  10. washElution with dichloromethane to 30% of ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-2443635f7ec142e29debb1b4f4b6487e
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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