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

HRID 1959574ノート

反応式

HRID 1959574 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-f9065cdd751d4ad9a80aad29af84d993
出典データセット
uspto-grants-2013_04
特許番号
US08410134B2

反応ノート

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