(+-)-2-Butanol → 2-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine

HRID 1506626

反応式

HRID 1506626 の反応式
[C:1]1([N:7]2[C:11]([C:12]#[N:13])=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([Mg]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(O)CC.[BH4-].[Na+]>O1CCCC1.CO>[C:15]1([CH2:14][CH:12]([C:11]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[N:9][CH:10]=2)[NH2:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 6568(+-)-2-ButanolHCID 4311764Sodium borohydrideHCID 846537091-phenyl-1H-1,2,3-triazole-5-carbonitrileHCID 178418336HCID 178418336、化合物

生成物 1

HCID 902812472-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 9C (280 mg, 1.63 mmol) in tetrahydrofuran (5 mL), benzylmagnesium chloride (2M in THF) (1.23 mL, 2.46 mmol) was added dropwise. After 3 hours, 3 mL of 2-butanol was added to the reaction and sodium borohydride (0.5 g) was added to the mixture by portion. The reaction was monitored by LC/Mass until it was done. Methanol (5 mL) was added to the mixture. The organic layer was washed with brine and extracted with ethyl acetate (50 mL twice). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was purified by flash column (Rf: 0.3, 3% MeOH/DCM) to provide the desired product. MS (m/z) 265 [M+H]+.

後処理

  1. additionwas added to the mixture by portion
  2. washThe organic layer was washed with brine
  3. extractionextracted with ethyl acetate (50 mL twice)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column (Rf: 0.3, 3% MeOH/DCM)

出典と根拠

ORDレコード
ord-55b96b07b7ae4eed898402a7696ec0dc
出典データセット
uspto-grants-2015_12
特許番号
US09220710B2

関連ノート

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