Sodium borohydride → rac-tert-Butyl ((1-benzyl-3-methyl-1,2,5,6-tetrahydropyridin-2-yl)methyl)carbamate

HRID 60988Notes

Reaction equation

HRID 60988 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]=[C:11]([CH3:15])[CH:10]1[CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89739374HCID 89739374, compound

Product 1

HCID 117732713rac-tert-Butyl ((1-benzyl-3-methyl-1,2,5,6-tetrahydropyridin-2-yl)methyl)carbamateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-2-(((tert-butoxycarbonyl)amino)methyl)-3-methylpyridin-1-ium bromide (10.9 g, 35 mmol) in MeOH (500 ml) was added NaBH4 (3.95 g, 104 mmol) in three portions at 0° C. The solution was then stirred for 3 h at rt and then concentrated in vacuo. The crude residue was taken up in EtOAc and washed with sat aq. NaHCO3, dried (MgSO4), and concentrated. The crude residue was purified by chromatography on silica gel (EtOAc/hexanes) to give the title compound as a pale yellow oil (6.67, 61%). MS (ESI) 317 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-8935876c667840d1994f962f4e2299a3
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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