Water → HCID 71279282, compound

HRID 246761Notes

Reaction equation

HRID 246761 reaction equation
CS(O[CH:6]1[CH2:11][CH:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][O:8][CH2:7]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+].O>CN(C)C=O>[N:20]([CH:6]1[CH2:7][O:8][CH2:9][CH:10]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11]1)=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86678015HCID 86678015, compound

Product 1

HCID 71279282HCID 71279282, compoundYield 137.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-3-yl methanesulfonate (90 mg, 0.3 mmol) and sodium azide (30 mg, 0.5 mmol) in 10 mL of dry N,N-dimethylformamide was heated to 100° C. for 3 h. The reaction mixture was cooled to room temperature, 40 mL of water were added, product extracted with ethyl acetate (2×50 mL), organics combined dried with sodium sulfate, filtered and concentrated to give tert-butyl 5-azido-tetrahydro-2H-pyran-3-ylcarbamate (100 mg, crude) which was used directly in the next step without further purification.

Workup

  1. extractionproduct extracted with ethyl acetate (2×50 mL)
  2. dry with materialorganics combined dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-96a66fab1dc24718bccd76bf002bb9ff
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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