Sodium borohydride → Benzylethanolamine

HRID 517656Notes

Reaction equation

HRID 517656 reaction equation
[CH:1](=[N:8]/[CH2:9][CH2:10][OH:11])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178521301HCID 178521301, compound

Product 1

HCID 4348BenzylethanolamineYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound 1 (2.62 g, 17.3 mmol) in anhydrous EtOH (55 mL) was portionwise added NaBH4 (0.67 g, 17.7 mmol) at 0° C. over 1 h period. The resulting mixture was gradually warmed to room temperature and was stirred for 20 h. The resulting mixture was filtered to eliminate excess NaBH4, and the solvent was evaporated. The residue was dissolved in CH2Cl2 (50 mL) and filtered, and the filtrate was concentrated in vacuo to afford Compound 2 (1.86 g, 61.3%). 1H NMR (CDCl3) δ 2.60 to 2.70 (m, 2H), 3.60 to 3.73 (m, 2H), 7.24 to 7.27 (m, 5H); 13C NMR (CDCl3) δ 50.62, 53.44, 60.45, 126.98, 128.11, 128.36, 139.73. HRMS (Positive ion FAB) Calcd for C9H13NO [M+H]+ m/z 152.2163. Found: [M+H]+ m/z 152.1075.

Workup

  1. customat 0° C.
  2. customover 1 h
  3. filtrationThe resulting mixture was filtered
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-64977a4fb33d429c9bc77f6ea645a6b4
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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