Acetic Acid → (1-cyclobutyl-piperidin-4-yl)-(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methanol

HRID 12473

反応式

HRID 12473 の反応式
[CH2:1]([N:3]1[CH:7]=[C:6]([CH:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])[N:5]=[C:4]1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[CH3:2].[C:26]1(=O)[CH2:29][CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C(Cl)Cl>[CH:26]1([N:13]2[CH2:12][CH2:11][CH:10]([CH:8]([C:6]3[N:5]=[C:4]([C:16]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH:19]=[CH:18][CH:17]=4)[N:3]([CH2:1][CH3:2])[CH:7]=3)[OH:9])[CH2:15][CH2:14]2)[CH2:29][CH2:28][CH2:27]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 59337926(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-piperidin-4-yl-methanol

生成物 1

HCID 59337851(1-cyclobutyl-piperidin-4-yl)-(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-piperidin-4-yl-methanol (0.53 g) in CH2ClCH2Cl (12 ml) is added cyclobutanone (0.95 ml), followed by NaBH(OAc)3 and acetic acid (0.1 ml). The resulting mixture is stirred at rt overnight, diluted with CH2Cl2, washed with Na2CO3 (1M), H2O and brine, dried and solvent removed. The crude is purified by column (2% Et3N, 3% MeOH in EtOAc) to afford the title compound as a white solid, LCMS 390.1 (M+1).

後処理

  1. washwashed with Na2CO3 (1M), H2O and brine
  2. customdried
  3. customsolvent removed
  4. customThe crude is purified by column (2% Et3N, 3% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-49b7772e7ec2441798f0cd7657c64a6c
出典データセット
uspto-grants-2010_06
特許番号
US07728009B1

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