Lithium Hydroxide → N-(2,2-Diphenyl-ethyl)-2-hydroxy-N-methyl-2-phenyl-acetamide

HRID 1064528노트

반응식

HRID 1064528 반응식
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][NH:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([ClH][C:21](=[O:30])[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[OH:23])(=O)C.C(N(CC)CC)C.[OH-].[Li+]>C(Cl)(Cl)Cl.O1CCCC1.CO>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][N:9]([CH3:10])[C:21](=[O:30])[CH:22]([OH:23])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 12914583N-Methyl-2,2-diphenylethan-1-amine

생성물 1

HCID 22174856N-(2,2-Diphenyl-ethyl)-2-hydroxy-N-methyl-2-phenyl-acetamide수율 93.5%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a stirred solution of (2,2-diphenylethyl)methylamine (4.97 g, 23.5 mmol) in chloroform (50 mL) was added O-acetylmandelic chloride (5.3 mL, 24 mmol) followed by triethylamine (4.0 mL, 29 mmol). The reaction was stirred for 1 hour and then concentrated. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a colorless gum. The crude amide was taken up in 1:1 tetrahydrofuran/methanol (80 mL) and treated with 1 N aqueous lithium hydroxide (30 mL, 30 mmol). The mixture was stirred for 2 hours and concentrated to remove the organic solvents. The remaining aqueous solution was diluted with water and extracted twice with ethyl acetate and once with methylene chloride. The combined organic extracts were dried (sodium sulfate) and concentrated to afford an off-white solid. This material was triturated with diethyl ether to afford 7.59 g (93%) of product as a white solid: 1H NMR (CDCl3) δ 7.43-6.98 (m, 15H), 5.07 (s, 1H), 4.57-4.44 (m, 1H), 4.36-4.28 (m, 1H), 3.76-3.64 (m, 1H), 2.46 (s, 3H) ppm.

후처리

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customto afford a colorless gum
  6. stirringThe mixture was stirred for 2 hours
  7. concentrationconcentrated
  8. customto remove the organic solvents
  9. additionThe remaining aqueous solution was diluted with water
  10. extractionextracted twice with ethyl acetate and once with methylene chloride
  11. dry with materialThe combined organic extracts were dried (sodium sulfate)
  12. concentrationconcentrated
  13. customto afford an off-white solid
  14. customThis material was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-88f33495c92c4b379abd340d5509069a
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969728B2

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