Potassium Carbonate → {4-[(3-Fluoro-pyridin-2-ylmethyl)-amino]-butyl}-methyl-carbamic acid tert-butyl ester

HRID 251070

反応式

HRID 251070 の反応式
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[C:17]([CH:22]=O)=[N:18][CH:19]=[CH:20][CH:21]=1.C([O-])([O-])=O.[K+].[K+].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:22][C:17]1[C:16]([F:15])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2756377N-(4-Aminobutyl)-N-methyl carbamic acid tert-butyl esterHCID 4311764Sodium borohydrideHCID 113440173-Fluoro-2-pyridinecarboxaldehyde

生成物 1

HCID 67271861{4-[(3-Fluoro-pyridin-2-ylmethyl)-amino]-butyl}-methyl-carbamic acid tert-butyl ester収率 74%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of (4-amino-butyl)-methyl-carbamic acid tert-butyl ester (0.202 g, 1.00 mmol), 3-fluoro-pyridine-2-carbaldehyde (0.125 g, 1.00 mmol) and K2CO3 (0.138 g, 1.00) in MeOH (5 mL) was stirred for 16 h. The mixture was filtered through a celite cake and NaBH4 (0.050 g, 1.3 mmol) was added to the filtrate, and the mixture was stirred for 30 min. Saturated aqueous NaHCO3 (20 mL) was added, and MeOH was removed. The aqueous residue was extracted with CH2Cl2 (3×30 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (50:2:1 CH2Cl2/MeOH/NH4OH), affording {4-[(3-fluoro-pyridin-2-ylmethyl)-amino]-butyl}-methyl-carbamic acid tert-butyl ester as a colorless oil (0.230 g, 74%). 1H NMR (CDCl3) δ 1.42 (s, 9H), 1.48-1.54 (m, 4H), 2.61-2.68 (m, 2H), 2.80 (s, 3H), 3.14-3.22 (m, 2H), 3.96 (s, 2H), 7.11-7.20 (m, 1H), 7.30-7.36 (m, 1H), 8.33-8.38 (m, 1H).

後処理

  1. additionwas added to the filtrate
  2. stirringthe mixture was stirred for 30 min
  3. customMeOH was removed
  4. extractionThe aqueous residue was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed by evaporation under vacuum
  8. customthe residue was purified by flash chromatography on a silica gel column (50:2:1 CH2Cl2/MeOH/NH4OH)

出典と根拠

ORDレコード
ord-c56fed248a64434cb85fd83a053f079e
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

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