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Trifluoroacetic acid → 1-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine

HRID 1108028
ノート
印刷プレビュー

反応式

HRID 1108028 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 187863061-Benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine

生成物 1

HCID 111106201-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine収率 67.7%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

The product of Step 2 (5.1 g) in CH2Cl2 (50 mL) was treated sequentially with trifluoroacetic acid (8.9 mL) and triethylsilane (34.5 mL). After 18 h, the solution was treated with saturated NaHCO3 (150 mL). After a further 1 h, the organic layer was separated and the aqueous extracted with CH2Cl2 (100 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography, eluting with EtOAc/hexane mixtures to give 1-benzyloxycarbonyl-4(2-methylthiophenyl)piperidine (3.3 g).

後処理

  1. waitAfter a further 1 h
  2. customthe organic layer was separated
  3. extractionthe aqueous extracted with CH2Cl2 (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with EtOAc/hexane

出典と根拠

ORDレコード
ord-4cb6fe4f100e44b4a103b7312aeb065d
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06063926

反応ノート

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