p-Toluenesulfonic acid monohydrate → HCID 23112193, compound

HRID 1373065Notes

Reaction equation

HRID 1373065 reaction equation
[CH2:1]([N:8]([CH:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[C:26]([CH:34]=[CH2:35])=[CH:27][N:28]=[CH:29]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.O.CO>[CH2:1]([N:8]([CH:16]1[CH2:21][CH2:20][CH:19]([NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[C:26]([CH:34]=[CH2:35])=[CH:27][N:28]=[CH:29]3)[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydrideHCID 15342642HCID 15342642, compoundHCID 23112198HCID 23112198, compound

Product 1

HCID 23112193HCID 23112193, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of Intermediate 9 (5.73 g), Intermediate 1 (2.92 g), and para-toluenesulfonic acid monohydrate (163 mg, Wako Pure Chemical Industries) in toluene (50 ml) was refluxed by heating for 1 hour. The reaction mixture was cooled to room temperature, then added with methanol (75 ml) and sodium borohydride (6.48 g), and stirred at room temperature for 1 hour. The reaction mixture was added with water (5 ml), and then the solvent was evaporated under reduced pressure. The residue was added with ethyl acetate (100 ml), and the organic layer was washed twice with water (50 ml), and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (2.2 g of trans-isomer, 1.8 g of cis-isomer).

Workup

  1. temperatureby heating for 1 hour
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added with ethyl acetate (100 ml)
  4. washthe organic layer was washed twice with water (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-41a3b8079b3f487787e7b5d409b75ded
Source dataset
uspto-grants-2007_01
Patent number
US07160894B2

Reaction notes

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