Ammonium Chloride → Tert-butyl 3-(5H-tetrazol-5-yl)morpholine-4-carboxylate

HRID 524758Notes

Reaction equation

HRID 524758 reaction equation
[C:1]([CH:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+]>CN(C=O)C.CCOC(C)=O>[N:16]1[CH:1]([CH:3]2[CH2:8][O:7][CH2:6][CH2:5][N:4]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[N:2]=[N:18][N:17]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21098190tert-Butyl 3-cyanomorpholine-4-carboxylate

Product 1

HCID 90043836Tert-butyl 3-(5H-tetrazol-5-yl)morpholine-4-carboxylateYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 3-cyanomorpholine-4-carboxylate (5 g, 23.6 mmol, the compound was synthesized according to the procedure as described in J. Med. Chem. 2007, 50(20), 4953-4975), sodium azide (1.53 g, 23.6 mmol) and ammonium chloride (0.63 g, 11.8 mmol) in anhydrous DMF (30 mL) was stirred at 100° C. for 72 hours and cooled to 25° C. The reaction mixture was diluted with EtOAc (300 mL), then washed with brine (150 mL×6). The organic phase was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=1/1) to give the title compound as a brownish solid (2.5 g, 41%). The compound was characterized by the following spectroscopic data:

Workup

  1. customthe compound was synthesized
  2. washwashed with brine (150 mL×6)
  3. concentrationThe organic phase was concentrated in vacuo
  4. customthe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=1/1)

Sources & evidence

ORD record
ord-41f446c4c2fc4c2a9e940dd12c5bce3e
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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