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Tetrahydro-4H-pyran-4-one → HCID 69122283、化合物

HRID 2064094
ノート
印刷プレビュー

反応式

HRID 2064094 の反応式
[ClH:1].[F:2][CH:3]([F:21])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:9]=2[CH:20]=1.[O:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.ClCCCl>[ClH:1].[F:21][CH:3]([F:2])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:15][CH2:16][N:17]([CH:25]4[CH2:26][CH2:27][O:22][CH2:23][CH2:24]4)[CH2:18][CH2:19]3)[C:9]=2[CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57423922HCID 57423922、化合物

生成物 1

HCID 69122283HCID 69122283、化合物収率 68.6%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane
溶媒
HCID 8471Triethylamine溶媒

実験手順

6-[(Difluoromethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D54, 0.3 g) 1,2-dichloroethane (10 ml) and triethylamine (0.5 ml), tetrahydro-4H-pyran-4-one (0.6 g), sodium triacetoxyborohydride (0.6 g) was stirred at room temperature over 3 days. The mixture was poured into sodium bicarbonate solution and extracted with dichloromethane. The organic phase was separated, washed with brine and the solvent was removed and the residue was chromatographed on silica gel eluted with dichloromethane/2M ammonia in methanol 0-10%. The resulting product was dissolved in a mixture of methanol and dichloromethane, treated with 1M hydrogen chloride in ether and the solvent was removed. Recrystallisation from methanol gave the title compound as a white solid (0.26 g). Mass Spectrum 368 M+H+

後処理

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customthe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. washeluted with dichloromethane/2M ammonia in methanol 0-10%
  7. dissolutionThe resulting product was dissolved in a mixture of methanol and dichloromethane
  8. additiontreated with 1M hydrogen chloride in ether
  9. customthe solvent was removed
  10. customRecrystallisation from methanol

出典と根拠

ORDレコード
ord-5b0e0ffdbf4e4ba996af0acf0883fa53
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08288413B2

反応ノート

読み込み中…

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