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

HRID 507287ノート

反応式

HRID 507287 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-32ad9ade040f44338dde7f120d64dc4b
出典データセット
uspto-grants-2010_08
特許番号
US07786143B2

反応ノート

読み込み中…