Sodium Bicarbonate → (9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate

HRID 522863노트

반응식

HRID 522863 반응식
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH:15]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH2:7][CH2:6]1)=O.[C:28]([NH2:36])(=[S:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>CCO>[C:29]1([C:28]2[S:35][CH:2]=[C:3]([CH:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][CH:15]4[C:27]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[C:21]5[C:16]4=[CH:17][CH:18]=[CH:19][CH:20]=5)=[O:12])[CH2:9][CH2:10]3)[N:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 683563ThiobenzamideHCID 86685241(9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate

생성물 1

HCID 67353898(9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate수율 61%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of (9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate (3 g, 7.03 mmol) in EtOH (20 mL) was added thiobenzamide (0.96 g, 7.03 mmol). This reaction mixture was stirred at RT for 24 h. NaHCO3 (3 g) was added and the reaction mixture was further stirred for 5 d. The reaction mixture was concentrated to afford the crude material which was chromatographed over silica gel eluting with a gradient (0-10% EtOAc:hexanes) to afford (9H-fluoren-9-yl)methyl 4-(2-phenylthiazol-4-yl)piperidine-1-carboxylate (2 g, 61%) as an off white solid.

후처리

  1. stirringthe reaction mixture was further stirred for 5 d
  2. concentrationThe reaction mixture was concentrated
  3. customto afford the crude material which
  4. customwas chromatographed over silica gel eluting with a gradient (0-10% EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-fec98cb7b66744eb92fa19de0b0b8e70
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

반응 노트

불러오는 중…