Methanol → tert-butyl N-{[3-(hydroxymethyl)-4-nitrophenyl]methyl}carbamate

HRID 862599ノート

反応式

HRID 862599 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:20]([O-:22])=[O:21])=[C:14]([CH:19]=1)[C:15](OC)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.S([O-])(O)(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:20]([O-:22])=[O:21])=[C:14]([CH:19]=1)[CH2:15][OH:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 887MethanolHCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 19698365Methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate

生成物 1

HCID 19698378tert-butyl N-{[3-(hydroxymethyl)-4-nitrophenyl]methyl}carbamate収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate (2.0 g, 6.45 mmol) and sodium borohydride (740 mg, 19.56 mmol) in THF (11 mL) was added dropwise methanol (1.5 mL) over 1.5 h under reflux. After the addition was completed, the excess reagent was decomposed with 5% aqueous potassium hydrogen sulfate. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 3:1 to 1:1 hexane/ethyl acetate to give 1.16 g of the title compound (64%).

後処理

  1. temperatureunder reflux
  2. additionAfter the addition
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with 3:1 to 1:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-2ec2bcbb0bc540d38d6cd1b8f1eddfb4
出典データセット
uspto-grants-1998_02
特許番号
US05719152

反応ノート

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