Triethylamine → (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

HRID 12401

반응식

HRID 12401 반응식
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19](O)=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

생성물 1

HCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol수율 89.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

O-benzyl-N-(t-butoxycarbonyl)-L-serine (2 g) was dissolved in tetrahydrofuran (20 ml), triethylamine (1.22 ml) was added, and ethyl chloroformate (713 μl) was further added dropwise at 0° C. After stirring the reaction mixture at room temperature for 30 min, the reaction mixture was filtered, and one piece of ice was added to the filtrate. Sodium borohydride (515 mg) was further added, and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate (1.7 g)

후처리

  1. filtrationthe reaction mixture was filtered
  2. additionone piece of ice was added to the filtrate
  3. additionSodium borohydride (515 mg) was further added
  4. stirringthe mixture was stirred at room temperature for 6 hrs
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washafter washing with water
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe obtained crude product
  10. customwas purified by silica gel chromatography (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-62c17d1cfb3e4e06b586c994edd4847a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728005B2

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