Ammonium Chloride → HCID 58745508, compound

HRID 1254408Notes

Reaction equation

HRID 1254408 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CO.O>[N:18]([C@H:1]1[C@H:6]([OH:7])[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]1)=[N+:19]=[N-:20]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13186888Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 58745508HCID 58745508, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (6.78 g, 29.1 mmol), sodium azide (3.78 g, 2 equiv), and ammonium chloride (1.56 g, 1 equiv) were dissolved in methanol (100 mL) and water (20 mL). The mixture was heated at 65° C. for 18 h. The mixture was cooled to rt and methanol was removed under vacuum. The aqueous residue was extracted with ether (3×120 mL). The combined ether layers were washed with brine (30 mL) and dried over Na2SO4. Concentration afforded (3R,4R)-benzyl 3-azido-4-hydroxypiperidine-1-carboxylate (8.07 g, quant.) which was used for without further purification. LC-MS (3 min) tR=1.45 min., m/z 277 (M+1).

Workup

  1. temperatureThe mixture was cooled to rt
  2. custommethanol was removed under vacuum
  3. extractionThe aqueous residue was extracted with ether (3×120 mL)
  4. washThe combined ether layers were washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration

Sources & evidence

ORD record
ord-fa9f4c5226e64d1083502e3f140193f0
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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