Phenylacetyl chloride → (4aRS,7aRS)-6-phenylacetyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole

HRID 375491

Reaction equation

HRID 375491 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:12]1([C:18]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:26]3[CH:22]([CH2:23][NH:24][CH2:25]3)[S:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[C:1]1([CH2:7][C:8]([N:24]2[CH2:25][CH:26]3[C:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:19][CH2:20][S:21][CH:22]3[CH2:23]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 67745331(4aRS,7aRS)4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride

Product 1

HCID 67745329(4aRS,7aRS)-6-phenylacetyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 1.15 cm3 of phenylacetyl chloride in 25 cm3 of dichloromethane is added over 5 minutes to a solution, cooled to 0° C., of 2.63 g of (4aRS,7aRS)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride and 2.42 cm3 of triethylamine in 25 cm3 of dichloromethane. After stirring for one hour at 0° C. and one hour at 20° C. 20 cm3 of dichloromethane are added. The reaction mixture is washed twice with 100 cm3 of distilled water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is chromatographed on a silica gel column (0.04-0.06 mm, diameter 3.5 cm, height 26 cm), eluting under a nitrogen pressure of 0.4 bar with a cyclohexane and ethyl acetate mixture (80/20 by volume) and collecting fractions of 125 cm3. Fractions 19 to 26 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 0.87 g of (4aRS,7aRS)-6-phenylacetyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole is obtained in the form of a white solid; melting point 210° C.

Workup

  1. washThe reaction mixture is washed twice with 100 cm3 of distilled water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe oil obtained
  5. customis chromatographed on a silica gel column (0.04-0.06 mm, diameter 3.5 cm, height 26 cm)
  6. washeluting under a nitrogen pressure of 0.4 bar with a cyclohexane and ethyl acetate mixture (80/20 by volume)
  7. customcollecting fractions of 125 cm3
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-91899b1311aa4244949fdaa59b28a98c
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Linked notes

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