Acetic Acid → HCID 86623722, compound

HRID 249914Notes

Reaction equation

HRID 249914 reaction equation
[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

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 136809Benzophenone imineHCID 5003444Sodium cyanoborohydride2×HCID 12526564HCID 12526564, compound

Product 1

HCID 86623722HCID 86623722, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e393bbe36fde42a08c14bdd1128e66dc
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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