Water → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

HRID 355464노트

반응식

HRID 355464 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([OH:14])=[O:13].[OH-].[Na+].O.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>CC(C)=O>[CH2:34]([O:33][C:31]([N:18]1[CH2:17][CH2:16][C:15]([C:12]([OH:14])=[O:13])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

생성물 1

HCID 227417981-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid수율 90.3%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
5 °C

실험 절차

A mixture of 37.7 g of 4-carboxy-4-phenylpiperidine p-toluenesulphonate, 53.3 g of 30% aqueous NaOH solution and 250 ml of water is cooled to 5° C. A solution of 18 g of benzyl chloroformate in 60 ml of acetone is added rapidly at 5° C., and the mixture is left stirring overnight while allowing the temperature to rise to RT. The reaction mixture is washed twice with ether and, after settling has taken place, the aqueous phase is separated and acidified to pH 1 by adding concentrated HCl and then 2N HCl. The precipitate formed is drained, dried, taken up in ether and drained again. 30.6 g of the expected product are obtained, m.p.=142°-144° C.

후처리

  1. waitthe mixture is left
  2. customto rise to RT
  3. washThe reaction mixture is washed twice with ether
  4. customthe aqueous phase is separated
  5. additionby adding concentrated HCl
  6. customThe precipitate formed
  7. customdried

출처 및 근거

ORD 기록
ord-9edd3216b4c04336a113c215dc3d42bf
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830906

반응 노트

불러오는 중…