Aluminium lithium hydride → tert-Butyl 3-(hydroxymethyl)benzyl(methyl)carbamate

HRID 2355282ノート

反応式

HRID 2355282 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:16]([O:15][C:13](=[O:14])[N:11]([CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=1)[CH3:12])([CH3:19])([CH3:17])[CH3:18]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 59700597Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

生成物 1

HCID 18470938tert-Butyl 3-(hydroxymethyl)benzyl(methyl)carbamate収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Dissolve 3-[(tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid methyl ester (1.70 g, 6.1 mmol) in tetrahydrofuran (60 mL) at 0° C. Add a 1M solution of lithium aluminum hydride in tetrahydrofuran (8 mL, 8 mmol) dropwise and stir for 2 hrs. Quench the reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL), filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 40-60% ethyl acetate/hexanes to provide the title compound (1.42 g, 93%).

後処理

  1. customQuench
  2. customthe reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by chromatography (silica gel)
  6. washeluting with 40-60% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-74b771b0f1ee4432b1714dfdda0ebe63
出典データセット
uspto-grants-2010_07
特許番号
US07754742B2

反応ノート

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