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

HRID 2407868Notes

Reaction equation

HRID 2407868 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e968d64233b040f493b5534871c4e592
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

Loading…