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

HRID 522863ノート

反応式

HRID 522863 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fec98cb7b66744eb92fa19de0b0b8e70
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

反応ノート

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