Acetic Acid → Tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate

HRID 1467963Notes

Reaction equation

HRID 1467963 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:15][C:16]1[N:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(OCC)(=O)C>[Br:15][C:16]1[N:21]=[CH:20][C:19]([NH:22][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6428116-Bromopyridin-3-amineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86602140Tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl 4-oxopiperidine-1-carboxylate (1.15 g, 5.78 mmol) and 6-bromopyridin-3-amine (0.5 g, 2.89 mmol) in dichloroethane (20 mL), acetic acid (8 mL, 2.89 mmol) was added and the contents were stirred at room temperature for 3 h. Sodium triacetoxy borohydride (1.225 g, 5.78 mmol) was added and the contents were stirred at room temperature for 12 h. The reaction was diluted with ethyl acetate and washed with brine; the organic layer was separated and concentrated in vacuo. The resulting residue was purified by flash column chromatography to give tert-butyl 4-((6-bromopyridin-3-yl)amino)piperidine-1-carboxylate (0.638 g, 62%); MS: 357.1 (M+1)

Workup

  1. additionwas added
  2. stirringthe contents were stirred at room temperature for 12 h
  3. washwashed with brine
  4. customthe organic layer was separated
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-095a9df2de08454da67543e86e1307a9
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

Loading…