Tetrabutylammonium Fluoride → [2-(2-Hydroxyethoxy)ethoxy]methylcarbamic acid tert-butyl ester

HRID 2093242

反応式

HRID 2093242 の反応式
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][N:31]([CH3:39])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])(C)(C)C>C1COCC1>[CH3:39][N:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][OH:24]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86643773O-{2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethoxy]-ethyl}-N-methyl-N-BOC-hydroxylamine

生成物 1

HCID 86643775[2-(2-Hydroxyethoxy)ethoxy]methylcarbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

TBAF (6.78 mL, 6.78 mmol) was added to O-{2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethoxy]-ethyl}-N-methyl-N-BOC-hydroxylamine (d) (3 g, 6.33 mmol) dissolved in dry THF (15 mL). The reaction was stirred over night. The THF was evaporated off and the residue was dissolved in DCM and washed with NH4Cl (saturated) (40 mL), water and brine. The organic phase was dried (MgSO4) and evaporated off. The residue was purified using flash chromatography on a Companion Combiflash 40 g column (Gradient MeOH 0-5% over 20 minutes in DCM. Structure confirmed by NMR.

後処理

  1. customThe THF was evaporated off
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with NH4Cl (saturated) (40 mL), water and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated off
  6. customThe residue was purified
  7. customover 20 minutes

出典と根拠

ORDレコード
ord-65ceeeb5788c4d60a7f0d86a84da181c
出典データセット
uspto-grants-2013_05
特許番号
US08444955B2

関連ノート

読み込み中…