Acetic Acid → 1-(Cyclohexylmethylamino)-2-propanol

HRID 2358902Notes

Reaction equation

HRID 2358902 reaction equation
[CH:1]1([NH:7][CH2:8][CH:9]([OH:11])[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:16](C)=O.[Na+].C(O)(=O)C>ClCCCl.C(OCC)(=O)C.[OH-].[Na+]>[CH:1]1([N:7]([CH3:16])[CH2:8][CH:9]([OH:11])[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 76302-Propanol, 1-(cyclohexylamino)-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 2776011-(Cyclohexylmethylamino)-2-propanol

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 1-(cyclohexylamino)-propan-2-ol (crude 2.6 g) in DCE (30 mL) were added successively HCHO (35% in water, 2.1 mL, 24.8 mmol), Na(OAc)3BH (10.5 g, 49.6 mmol) and acetic acid (1 mL) at ice-cold conditions. The resulting mixture was allowed to stir at rt for 16 hours. The reaction was diluted with ethyl acetate and basified with 1N NaOH. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on silica-gel (230-400 mesh) eluting with 5% MeOH/DCM to provide 1-(cyclohexyl(methyl)amino)propan-2-ol. Yield: 1.0 g 1H NMR (DMSO-d6) δ 4.11 (brs, 1 H), 3.65-3.57 (m, 1 H), 2.35-2.20 (m, 3 H), 2.19 (s, 3 H), 1.72-1.68 (m, 4 H), 1.57-1.54 (m, 1 H), 1.24-1.05 (m, 5 H), 1.01 (d, J=6 Hz, 3 H).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography on silica-gel (230-400 mesh)
  7. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-33bf0ff1cb054590bd6e40976ffcb724
Source dataset
uspto-grants-2014_04
Patent number
US08685418B2

Reaction notes

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