Acetic Acid → HCID 68951075、化合物

HRID 2384931ノート

反応式

HRID 2384931 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:15](O)(=O)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11]2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68953107HCID 68953107、化合物

生成物 1

HCID 68951075HCID 68951075、化合物収率 68.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution (4-bromo-phenyl)-pyrrolidin-3-yl-methanone (2.24 g, 8.81 mmol) in methanol (44 mL), add acetic acid (1.01 mL, 17.6 mmol) and formaldehyde (2.15 g, 26.4 mmol, 37% aqueous solution). After 15 min, add sodium triacetoxyborohydride (5.60 g, 26.4 mmol) and allow the mixture to stir at RT for one hour. Concentrate the reaction mixture. Add water and adjust the solution to pH=10 with 2 N NaOH. Extract the aqueous with ethylacetate. Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 5-10% MeOH (2N NH3)/CH2Cl2 to give 1.61 g (68%) of the title compound. LC-MS/ES m/z (79Br) 268.0 [M+H]+.

後処理

  1. concentrationConcentrate the reaction mixture
  2. extractionExtract the aqueous with ethylacetate
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude material by flash chromatography
  7. washeluting with 5-10% MeOH (2N NH3)/CH2Cl2

出典と根拠

ORDレコード
ord-240f835fc26849b18f937084b70199d9
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

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