Acetic Acid → HCID 86623722、化合物

HRID 249914ノート

反応式

HRID 249914 の反応式
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[NH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(O)=O.[OH-].[K+].[S:21]([CH2:26][C:27](=O)[CH3:28])[CH2:22][C:23](=O)[CH3:24].[BH3-]C#N.[Na+]>CO>[CH:7]([N:8]1[C@H:27]([CH3:28])[CH2:26][S:21][CH2:22][C@H:23]1[CH3:24])([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 136809Benzophenone imineHCID 5003444Sodium cyanoborohydride2 回HCID 12526564HCID 12526564、化合物

生成物 1

HCID 86623722HCID 86623722、化合物収率 13%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a stirred solution of diphenylmethanimine (2.36 mL, 13.7 mmol), HOAc (0.86 mL, 15.1 mmol), and potassium hydroxide (0.19 g, 3.4 mmol) in CH3OH (25 mL) cooled to 0° C. was added a solution of 1,1′-thiodipropan-2-one (2.0 g, 13.7 mmol) in CH3OH (10 mL). NaCNBH3 (0.86 g, 13.7 mmol) was then added and the reaction mixture stirred at ambient temperature for 16 h. A further portion of NaCNBH3 (0.43 g, 6.9 mmol) was added and the reaction mixture stirred for another 4 h. The reaction mixture was partitioned with EtOAc (150 mL) and H2O (150 mL) and the layers separated. The organic layer was washed with H2O (150 mL), brine (150 mL) then dried over Na2SO4. After concentration under reduced pressure, the resulting residue was purified by flash column chromatography (silica gel, 10-50% EtOAc in hexanes) to afford (3S,5S)/(3R,5R)-4-benzhydryl-3,5-dimethylthiomorpholine (0.52 g, 13%). 1H NMR consistent.

後処理

  1. stirringthe reaction mixture stirred for another 4 h
  2. customThe reaction mixture was partitioned with EtOAc (150 mL) and H2O (150 mL)
  3. customthe layers separated
  4. washThe organic layer was washed with H2O (150 mL), brine (150 mL)
  5. dry with materialthen dried over Na2SO4
  6. concentrationAfter concentration under reduced pressure
  7. customthe resulting residue was purified by flash column chromatography (silica gel, 10-50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-e393bbe36fde42a08c14bdd1128e66dc
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

反応ノート

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