(2S,5S)-2,5-dimethylpiperazine → (2s,5s)-1-(4-Bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

HRID 1602913

반응식

HRID 1602913 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:10]=2)=[CH:4][CH:3]=1.[CH3:24][C@H:25]1[CH2:30][NH:29][C@@H:28]([CH3:31])[CH2:27][NH:26]1.N[C@H](C(N[C@H](C(O)=O)C)=O)C.O=C1NCCNC1=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:26]2[CH2:27][C@H:28]([CH3:31])[NH:29][CH2:30][C@@H:25]2[CH3:24])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:10]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 61380(2S,5S)-2,5-dimethylpiperazineHCID 22350043alpha-(4-Bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chlorideHCID 131720131L-Ala-L-Ala diketopiperazine

생성물 1

HCID 57043709(2s,5s)-1-(4-Bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine수율 39%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The crude benzhydryl chloride (approx. 42 mmol) was combined with 9.55 g (84 mmol) of (+)-(2S,5S)-2,5-dimethylpiperazine, prepared from L-Ala-L-Ala-diketopiperazine (Bachem Chemicals, Philadelphia, Pa.) as described in J. Org. Chem. 50: 4909-13 (1985), and 30 mL of toluene and heated at reflux overnight under nitrogen. The toluene was removed under vacuum, and the residue was redissolved in diethyl ether and washed with 1.0 M sodium hydroxide followed by saturated aqueous sodium chloride. The ether solution was dried over sodium sulfate and the solvent removed to give a dark oil. The product was purified by chromatography on silica gel (Waters Prep 500) with 0.5-0.7% ethanol in dichloromethane with 0.1% triethylamine to give 8.01 g (39%) of (2S,5S)-1-(4-bromo-α-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine as a 1:1 mixture of diastereomers.

후처리

  1. temperatureat reflux overnight under nitrogen
  2. customThe toluene was removed under vacuum
  3. dissolutionthe residue was redissolved in diethyl ether
  4. washwashed with 1.0 M sodium hydroxide
  5. dry with materialThe ether solution was dried over sodium sulfate
  6. customthe solvent removed
  7. customto give a dark oil
  8. customThe product was purified by chromatography on silica gel (Waters Prep 500) with 0.5-0.7% ethanol in dichloromethane with 0.1% triethylamine

출처 및 근거

ORD 기록
ord-901068fd391a49e8b2feaf7a44c022d2
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05985880

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