Sodium borohydride → 1-(Benzyl-methyl-amino)-heptan-3-ol

HRID 2218084Notes

Reaction equation

HRID 2218084 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]([CH3:19])[CH2:11][CH2:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]([CH3:19])[CH2:11][CH2:12][CH:13]([OH:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 179819221-(Benzyl-methyl-amino)-heptan-3-one

Product 1

HCID 179819331-(Benzyl-methyl-amino)-heptan-3-olYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (1.29 g, 34.1 mmol) to a stirred solution of 1-(benzyl-methyl-amino)-heptan-3-one (2.41 g, 10 mmol) and methanol (45 ml) at 0° C. under N2. Stir the reaction for 1 hr at 0° C. Quench the reaction with water at 0° C. and concentrate under reduced pressure. Dissolve the residue in ethyl acetate, wash with brine and dry over sodium sulfate. Filter off and concentrate to give the crude compound. Purify the compound by flash chromatography, eluting with 5% ethanol/0.5% ammonium hydroxide/chloroform to yield 2.22 g (91%) of 1-(benzyl-methyl-amino)-heptan-3-ol: mass spectrum (ion spray) m/z=236 (M+1); 1H NMR (CDCl3) δ 7.34-7.23 (m, 5H), 3.76-3.72 (m, 1H), 3.53 (dd, 2H), 2.80-2.73 (m, 1H), 2.59-2.53 (m, 1H), 2.21 (s, 1H), 1.68-1.62 (m, 1H), 1.57-1.29 (m, 7H), 0.91 (t, 3H).

Workup

  1. customthe reaction for 1 hr at 0° C
  2. customQuench
  3. customthe reaction with water at 0° C.
  4. concentrationconcentrate under reduced pressure
  5. dissolutionDissolve the residue in ethyl acetate
  6. washwash with brine
  7. dry with materialdry over sodium sulfate
  8. filtrationFilter off
  9. concentrationconcentrate
  10. customto give the crude compound
  11. customPurify the compound by flash chromatography
  12. washeluting with 5% ethanol/0.5% ammonium hydroxide/chloroform

Sources & evidence

ORD record
ord-dd5e5857446a4c529895b9f3b241ea9c
Source dataset
uspto-grants-2008_08
Patent number
US07410982B2

Reaction notes

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