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

HRID 1827680ノート

反応式

HRID 1827680 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+]>C1COCC1>[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 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-4 (422 mg, 1.92 mmol) in THF 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 H20 (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 4-5 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-6494239def074b9dae0b4b18ce242276
出典データセット
uspto-grants-2006_06
特許番号
US07056909B2

反応ノート

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