Acetone → 4-(4-Phenyl-1,3-thiazol-2-yl)-1-(propan-2-yl)piperidine

HRID 507287노트

반응식

HRID 507287 반응식
Br.[C:2]1([C:8]2[N:9]=[C:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[S:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:22])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1COCC1.C(O)(=O)C.CCN(CC)CC.CO>[CH:20]([N:16]1[CH2:17][CH2:18][CH:13]([C:10]2[S:11][CH:12]=[C:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:9]=2)[CH2:14][CH2:15]1)([CH3:22])[CH3:19]

참가 물질

9

반응물 4

HCID 180AcetoneHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 684624534-(4-Phenyl-thiazol-2-yl)-piperidine hydrobromide

생성물 1

HCID 160618524-(4-Phenyl-1,3-thiazol-2-yl)-1-(propan-2-yl)piperidine

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

A mixture of 24.5 mg (0.1 mmol) 4-(4-phenyl-thiazol-2-yl)-piperidine hydrobromide, excess acetone and excess sodium triacetoxyborohydride in 1 ml THF and 20 μl acetic acid was stirred at room temperature for 16 h. After addition of 0.2 ml water, 0.2 ml methanol and 0.15 ml NEt3 the mixture was purified by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water (0.1% NEt3) to yield after evaporation of the product fractions 12.8 mg (45 %) of the title compound. (m/e): 287.3 (MH+; 100%).

후처리

  1. customwas purified by preparative HPLC on reversed phase
  2. washeluting with a gradient of acetonitrile/water (0.1% NEt3)
  3. customto yield
  4. customafter evaporation of the product fractions 12.8 mg (45 %) of the title compound

출처 및 근거

ORD 기록
ord-32ad9ade040f44338dde7f120d64dc4b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786143B2

반응 노트

불러오는 중…