9-Borabicyclo(3.3.1)nonane → 5-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

HRID 2187371ノート

反応式

HRID 2187371 の反応式
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[CH:7]=[CH2:8])[CH3:2].B1C2CCCC1CCC2.C([O-])(O)=[O:27].[Na+]>O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[CH2:7][CH2:8][OH:27])[CH3:2]

参加物

5

反応物 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 516892Sodium BicarbonateHCID 235812733-(2-Methyl-pyrimidin-5-yl)-pent-4-enoic acid ethyl ester

生成物 1

HCID 235812815-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of 2-4 (422 mg, 1.92 mmol) in TBF was added 5.75 mL of 9-BBN (0.5 M/THF). After 18 hours, a slurry of NaBO3 (2.35 g) and NaHCO3 (2.42 g) in H2O (10 mL) was added and the mixture stirred vigorously for 1 hour. The mixture was extracted with CHCl3, washed with brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 3% EtOH/EtOAc) to give 2-5 as a clear oil.

後処理

  1. extractionThe mixture was extracted with CHCl3
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customremoval of the solvent
  5. customthe residue was chromatographed (silica gel, 3% EtOH/EtOAc)

出典と根拠

ORDレコード
ord-e7e0fb571f0f429b886488fbbd45b041
出典データセット
uspto-grants-2002_06
特許番号
US06410526B1

反応ノート

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