Acetic Acid → HCID 86623722, 화합물

HRID 249914노트

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HRID 249914 반응식
[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

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 136809Benzophenone imineHCID 5003444Sodium cyanoborohydride2회HCID 12526564HCID 12526564, 화합물

생성물 1

HCID 86623722HCID 86623722, 화합물수율 13%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e393bbe36fde42a08c14bdd1128e66dc
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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