Triethylamine → 3-Dipropylamino-5-methyloxycarbonylchroman

HRID 37647ノート

反応式

HRID 37647 の反応式
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2S(C(F)(F)F)(=O)=O)[O:7][CH2:6]1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CN(C)[CH:63]=[O:64].[CH3:66][OH:67]>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:66]([O:64][CH3:63])=[O:67])[O:7][CH2:6]1)[CH2:2][CH3:3]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 19028106HCID 19028106、化合物HCID 21901440N,N-dimethylformamide methanol

生成物 1

HCID 190280933-Dipropylamino-5-methyloxycarbonylchroman収率 76%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

3-Dipropylamino-5-trifluoromethanesulfonylchroman (Example 1; 4.43 g, 11.6 mmol) was dissolved in 80 mL dimethylformamide/methanol 6:2 and the solution was degassed (10 mm Hg, 20° C., 15 min). PdOAc2 (76 mg, 0.34 mmol), 1,3-bis-diphenylphosphinopropane (141 mg, 0.34 mmol) and triethylamine (3.5 mL, 25 mmol) were then added. The mixture was heated to 70° C. under CO atmosphere and stirred for 5 hours. The solution was cooled, diluted with toluene (200 mL), washed with aqueous NaHCO3, dried with Na2SO4 and evaporated to dryness. The oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8. Yield: 76%, Mp 150°-152° C. (HCl-salt).

後処理

  1. customthe solution was degassed (10 mm Hg, 20° C., 15 min)
  2. temperatureThe solution was cooled
  3. washwashed with aqueous NaHCO3
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8

出典と根拠

ORDレコード
ord-0595e6bda57d4d278a420e53759717b1
出典データセット
uspto-grants-1995_05
特許番号
US05420151

反応ノート

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