Dimethyl Sulfoxide → HCID 11780885, 화합물

HRID 1199354노트

반응식

HRID 1199354 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][C@H:12]1[C@H:17]([C:18]2[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:19]=2[O:28][CH3:29])[CH2:16][CH2:15][N:14]([CH3:30])[CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O.C(N(CC)CC)C>[CH3:30][N:14]1[CH2:15][CH2:16][CH:17]([C:18]2[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:19]=2[O:28][CH3:29])[C:12](=[O:11])[CH2:13]1

참가 물질

8

반응물 4

HCID 679Dimethyl SulfoxideHCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 68880556HCID 68880556, 화합물

생성물 1

HCID 11780885HCID 11780885, 화합물수율 76.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

반응 조건

온도
-30 °C

실험 절차

Dimethyl sulfoxide (35 ml) is added dropwise under nitrogen to a solution, cooled to -60° C., of oxalyl chloride (20 ml) in dry methylene chloride (500 ml), and the mixture is stirred for 5-10 minutes. A solution of (±)-trans-3-hydroxy-4-(2,4,6-trimethoxyphenyl)-1-methylpiperidine (62 g) in methylene chloride (300 ml) is then added, while the temperature of the reaction mixture is held at -60° C. After the addition, the mixture is stirred for 15 minutes and triethylamine (155 ml) is added. The reaction mixture is then allowed to warm to a temperature of -30° C., diluted with water and rendered alkaline with sodium carbonate. The organic layer is separated off and the aqueous layer is extracted with ethyl acetate. The organic layers are combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give a solid residue which, on crystallization from isopropanol, gives the desired product (47 g) of melting point 110°-112° C.

후처리

  1. customis held at -60° C
  2. additionAfter the addition
  3. stirringthe mixture is stirred for 15 minutes
  4. customThe organic layer is separated off
  5. extractionthe aqueous layer is extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto give a solid residue which
  10. customon crystallization from isopropanol

출처 및 근거

ORD 기록
ord-a3302428993942ed846b47a39a5c4df0
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04900727

반응 노트

불러오는 중…