Potassium Carbonate → HCID 67745324, compound

HRID 375483Notes

Reaction equation

HRID 375483 reaction equation
[C:1]1([C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][S:10](=[O:14])(=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH2:26][N:27]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:28][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.ClCCl>[CH2:33]([N:27]1[CH2:28][CH:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:11][S:10](=[O:14])(=[O:13])[CH:9]2[CH2:26]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine2×HCID 67745317HCID 67745317, compound

Product 1

HCID 67745324HCID 67745324, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

2 drops of trifluoroacetic acid are added to a solution of 1.3 g of 3,4-dihydro-4,4-diphenyl-2H-thiapyran 1,1-dioxide and 1.75 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 12 cm3 of anhydrous dichloromethane, and the mixture is stirred for 30 minutes at 30° C. 1.75 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine and 2 drops of trifluoroacetic acid are again added and the mixture is stirred for 2 hours at 35° C. This last procedure is once again repeated and after stirring for 1 hour, 1 g of potassium carbonate is added. The suspension is filtered and the filtrate concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 3.2 cm, height 35 cm), eluting under a nitrogen pressure of 0.5 bar with a cyclohexane and ethyl acetate mixture (80/20 by volume) and collecting fractions of 30 cm3. Fractions 20 to 28 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 0.7 g of (4aRS,7aRS)-6-benzyl4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1,1-dioxide is obtained in the form of white crystals; melting point 186° l C.

Workup

  1. stirringthe mixture is stirred for 2 hours at 35° C
  2. stirringafter stirring for 1 hour
  3. filtrationThe suspension is filtered
  4. concentrationthe filtrate concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 3.2 cm, height 35 cm)
  6. washeluting under a nitrogen pressure of 0.5 bar with a cyclohexane and ethyl acetate mixture (80/20 by volume)
  7. customcollecting fractions of 30 cm3
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-8d34b91f51fd4038bd40c558d6ca0711
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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