Water → (2R)-3-(benzyloxy)-2-(tritylamino)propan-1-ol

HRID 221569노트

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HRID 221569 반응식
[CH2:1]([O:8][CH2:9][C@@H:10]([C:31](OC)=[O:32])[NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:31][OH:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67156483methyl O-benzyl-N-trityl-L-serinate

생성물 1

HCID 67156691(2R)-3-(benzyloxy)-2-(tritylamino)propan-1-ol수율 100.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

Methyl O-benzyl-N-trityl-L-serinate (2.94 g, 6.52 mmol) was dissolved in 100 mL of anhydrous Et2O and the solution was cooled to 0° C. under N2. Lithium aluminum hydride (1.63 g, 42.9 mmol) was added and the mixture was stirred for 90 minutes. The reaction mixture was then sequentially treated with 1.63 mL of H2O, 1.63 mL of 15% NaOH solution and 4.90 mL of H2O. After stirring for 30 minutes, the reaction mixture was filtered to remove the white solid. The solid was washed with several portions of Et2O and the combined filtrates were concentrated under reduced pressure. Chromatography (SiO2, 15-20% ethyl acetate/hexanes) gave 2.78 g of (2R)-3-(benzyloxy)-2-(tritylamino)propan-1-ol as a colorless oil.

후처리

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe reaction mixture was filtered
  3. customto remove the white solid
  4. washThe solid was washed with several portions of Et2O
  5. concentrationthe combined filtrates were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a93f7366cfac42a7ba5ae2f28c6774b4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207162B2

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