1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-Azidomethyl-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine

HRID 1959574Notes

Reaction equation

HRID 1959574 reaction equation
[Cl:1][C:2]1[C:3]([CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.C1(OP([N:34]=[N+:35]=[N-:36])(=O)OC2C=CC=CC=2)C=CC=CC=1.N1CCCN2CCCCCC=12>C1(C)C=CC=CC=1>[N:34]([CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 44190475[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methanol

Product 1

HCID 441904763-Azidomethyl-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of [5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methanol (1.3 g, 4.9 mmol), phosphorazidic acid diphenyl ester (1.4 mL, 6.4 mmol) and 2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine (0.96 mL, 6.4 mmol) in toluene (0.15 mL) was stirred at RT overnight. Solvents were concentrated in vacuo and the residue was partitioned between DCM (10 mL) and saturated NaCl solution (10 mL). After extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with hexanes/EA 3:1) to give the title compound. MS (m/z): 282.9 [M+H+].

Workup

  1. concentrationSolvents were concentrated in vacuo
  2. customthe residue was partitioned between DCM (10 mL) and saturated NaCl solution (10 mL)
  3. extractionAfter extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (elution with hexanes/EA 3:1)

Sources & evidence

ORD record
ord-f9065cdd751d4ad9a80aad29af84d993
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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