Sodium triacetoxyborohydride → HCID 45378004, compound

HRID 1630758Notes

Reaction equation

HRID 1630758 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.[BH-](O[C:31]([CH3:33])=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:8][C@@H:7]([C:31]2[CH:33]=[CH:12][CH:11]=[CH:4][CH:3]=2)[CH3:6])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 58443276HCID 58443276, compound

Product 1

HCID 45378004HCID 45378004, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

R-α-Methyl benzylamine (0.12 mL, 0.928 mmol) and 6-methoxy-5-(4-(trifluoromethyl)phenyl)-3-pyridinecarbaldehyde (0.261 g, 0.928 mmol) were dissolved in 3.0 mL of 1,2-dichloroethane in a 10 mL round bottom flask. The solution was allowed to stir at 25° C. for 1 h, at which point NaBH(OAc)3 (0.295 g, 1.39 mmol) was added in one portion. The reaction was then stirred for 16 h at 25° C. The reaction was quenched by adding 5N NaOH (1.5 mL) and stirring vigorously for 30 min. The layers were separated and the aqueous layer was washed with DCM (3×2.0 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to give crude product, which was then purified by silica gel chromatography (1:1 hexane-EtOAc) to afford (1R)—N-((6-methoxy-5-(4-(trifluoromethyl)phenyl)-3-pyridinyl)methyl)-1-phenylethanamine 1. MS m/z: 387 (MH+).

Workup

  1. additionwas added in one portion
  2. customThe reaction was quenched
  3. additionby adding 5N NaOH (1.5 mL)
  4. stirringstirring vigorously for 30 min
  5. customThe layers were separated
  6. washthe aqueous layer was washed with DCM (3×2.0 mL)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude product, which
  11. customwas then purified by silica gel chromatography (1:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-3cb6cef3373646dfa32556311e290a73
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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