Methanol → tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate

HRID 1392379Notes

Reaction equation

HRID 1392379 reaction equation
O=C1[CH:8]2[CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7]2.C[OH:17].[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+]>O>[N:20]([CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH:8]1[OH:17])=[N+:21]=[N-:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69313017HCID 69313017, compound

Product 1

HCID 21874176tert-Butyl 4-azido-3-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of tert-butyl 7-oxo-3-azabicyclo[4.1.0]heptane-3-carboxylate (180.6 g, 0.60 mol) obtained in Step 2 in a mixed solvent of 700 ml of methanol and 100 ml of water, were added ammonium chloride (NH4Cl; 64.0 g, 1.2 mol) and sodium azide (NaN3; 98.0 g, 1.5 mol). The reaction mixture was refluxed for 8 hours and evaporated under reduced pressure to remove methanol. The resulting residue was extracted with ethyl acetate and then dried on magnesium sulfate. The resulting residue was purified with column chromatography to give the titled compound (62.0 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customevaporated under reduced pressure
  3. customto remove methanol
  4. extractionThe resulting residue was extracted with ethyl acetate
  5. customdried on magnesium sulfate
  6. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-140ee90714e04eb4a34b02b9fb4afcb9
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

Loading…