Tetrabutylammonium Fluoride → (S)-2-azido-3-(hexadecyloxy)propan-1-ol

HRID 2204972ノート

反応式

HRID 2204972 の反応式
[N:1]([C@H:4]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:5][O:6][Si](C(C)(C)C)(C)C)=[N+:2]=[N-:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOCC>[N:1]([C@H:4]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:5][OH:6])=[N+:2]=[N-:3]

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86678273(R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

生成物 1

HCID 86678274(S)-2-azido-3-(hexadecyloxy)propan-1-ol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane (1 eq), and 1M TBAF in THF (1.1 eq) in THF (0.2 M) was stirred at 25° C. for 20 minutes. The reaction was diluted with Et2O and washed with saturated NH4Cl, H2O, and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-30% EtOAc/Hex to give (S)-2-azido-3-(hexadecyloxy)propan-1-ol as a colorless oil.

後処理

  1. washwashed with saturated NH4Cl, H2O, and brine
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated en vaccuo
  4. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-8fe1607a277e4924a91a905b15d30082
出典データセット
uspto-grants-2016_06
特許番号
US09365506B2

反応ノート

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