Formaldehyde → 5-[(3,3-Difluoro-1-pyrrolidinyl)methyl]-1-[4-(trifluoromethyl)phenyl]-1H-tetrazole

HRID 517750ノート

反応式

HRID 517750 の反応式
Cl.[F:2][C:3]1([F:8])[CH2:7][CH2:6][NH:5][CH2:4]1.C=O.C([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])C.C[Si]([N:22]=[N+:23]=[N-:24])(C)C.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:32]=CC([N+]#[C-])=[CH:29][CH:28]=1>CO>[F:2][C:3]1([F:8])[CH2:7][CH2:6][N:5]([CH2:17][C:16]2[N:13]([C:14]3[CH:15]=[CH:32][C:27]([C:26]([F:36])([F:35])[F:25])=[CH:28][CH:29]=3)[N:24]=[N:23][N:22]=2)[CH2:4]1

参加物

7

反応物 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 78378AzidotrimethylsilaneHCID 27594124-(Trifluoromethyl)phenyl isocyanideHCID 249034823,3-Difluoropyrrolidine hydrochloride

生成物 1

HCID 565999415-[(3,3-Difluoro-1-pyrrolidinyl)methyl]-1-[4-(trifluoromethyl)phenyl]-1H-tetrazole収率 84%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3,3-difluoropyrrolidine hydrochloride (129 mg, 0.90 mmol, Sigma-Aldrich), formaldehyde (37%, aqueous, 0.067 mL, 0.9 mmol) and triethylamine (0.125 mL, 0.900 mmol) in methanol (4 mL) was stirred at room temperature for 1.5 h. Trimethylsilyl azide (0.155 mL, 1.170 mmol) and 4-(trifluoromethyl)phenyl isocyanide (200 mg, 1.170 mmol) were added and the reaction mixture stirred for 2 days at room temperature. The solution was concentrated in vacuo. The resulting residue was purified using MDAP. Fractions containing product were combined and concentrated in vacuo. The resulting solid was redissolved in MeOH and passed through a 5 g NH2 ion exchange column to give the title compound as a white solid (252 mg).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customThe resulting residue was purified
  3. additionFractions containing product
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting solid was redissolved in MeOH

出典と根拠

ORDレコード
ord-6113cb89da444810a026177ea6e7a02a
出典データセット
uspto-grants-2015_08
特許番号
US09115132B2

反応ノート

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