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

HRID 2355282노트

반응식

HRID 2355282 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-74b771b0f1ee4432b1714dfdda0ebe63
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754742B2

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