Hydrochloric Acid → HCID 178451554, compound

HRID 1096916Notes

Reaction equation

HRID 1096916 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][C:6]2=[O:25])#[N:2].[N-:26]=[N+:27]=[N-:28].[Na+].Cl.C(N(CC)CC)C.Cl>CCOC(C)=O.CN(C=O)C>[O:25]=[C:6]1[C:5]2[C:22](=[CH:23][CH:24]=[C:3]([C:1]3[NH:28][N:27]=[N:26][N:2]=3)[CH:4]=2)[O:21][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 66649586Tert-butyl 6-cyano-4-oxo-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]-1'-carboxylate

Product 1

HCID 178451554HCID 178451554, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 23 g of tert-butyl 6-cyano-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (67.17 mmol), 13.10 g sodium azide (201.52 mmol), 27.74 g of triethylamine hydrochloride (201.52 mmol), and 460 mL of dry DMF was stirred under a nitrogen atmosphere at 100° C. for 12 hours. After cooling to room temperature, 506 mL of EtOAc were added, followed by 322 mL of 1M HCl (322 mmol). Alternatively, 0.5M HCl maybe added until pH=3. The resulting layers were separated, the organic layer was washed with water/methanol (115 mL/46 mL), and then concentrated to give tert-butyl 4-oxo-6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidine]-1′-carboxylate.

Workup

  1. customThe resulting layers were separated
  2. washthe organic layer was washed with water/methanol (115 mL/46 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c6327e036f2f4a53b4ad85616d078d78
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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