Lauric Acid → 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

HRID 2395713ノート

反応式

HRID 2395713 の反応式
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.[Si:21]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[O:14]=[C:1]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[CH2:30]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

7

反応物 4

HCID 3893Lauric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223524143-((Tert-butyldimethylsilyl)oxy)piperidine

生成物 1

HCID 189895461-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

Dissolve lauric acid (0.77 g) in methylene chloride (50mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add, by dropwise addition, to a solution of 3-(O-tert-butyldimethylsilyloxy)piperidine (0.76 g, 3.5 mmol) and triethylamine (1 mL) in methylene chloride (20 mL). Stir overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid, and once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine.

後処理

  1. temperatureAllow to warm to room temperature
  2. stirringStir overnight
  3. customseparate the organic phase
  4. washWash twice with 10% sodium hydroxide, once with 10% hydrochloric acid
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo

出典と根拠

ORDレコード
ord-09da1355281f47208f3af32d81f56483
出典データセット
uspto-grants-1996_02
特許番号
US05489600

反応ノート

読み込み中…