Formaldehyde → 5-Benzyloxy-2-[2-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-2H-pyridazin-3-one

HRID 564188ノート

反応式

HRID 564188 の反応式
C(O[C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][CH2:19][N:20]3[C:25](=[O:26])[CH:24]=[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:22]=[N:21]3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(O)(=O)C>[CH2:28]([O:27][C:23]1[CH:22]=[N:21][N:20]([CH2:19][CH2:18][C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][CH2:17][N:8]([CH3:6])[CH2:9]3)=[CH:14][CH:13]=2)[C:25](=[O:26])[CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

7

反応物 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 670069227-[2-(4-Benzyloxy-6-oxo-6H-pyridazin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

生成物 1

HCID 580427265-Benzyloxy-2-[2-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-2H-pyridazin-3-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 90 mg (0.25 mmol) 5-benzyloxy-2-[2-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-2H-pyridazin-3-one (example 25.1) in 2.0 mL THF is added 28 μL (0.37 mmol) aqueous 37% formaldehyde solution. The mixture is acidified with 2 drops of acetic acid and then 79 mg (0.37 mmol) sodium triacetoxy-borohydride is added. The reaction mixture is stirred 2 h at RT and is poured into aqueous 10% Na2CO3-solution, the layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The residue is dissolved in DMF and is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

後処理

  1. customthe layers are separated
  2. extractionthe aqueous phase is extracted with EtOAc
  3. washThe combined organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. dissolutionThe residue is dissolved in DMF
  8. customis purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

出典と根拠

ORDレコード
ord-ad9b2704696c41cc8258e3b2fc691561
出典データセット
uspto-grants-2011_11
特許番号
US08067590B2

反応ノート

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