Sodium Hydroxide → (1R*,4aR*,7aR*)-(+)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide

HRID 375478Notes

Reaction equation

HRID 375478 reaction equation
[OH-].[Na+].C(O)(=O)[C@H](C1C=CC=CC=1)O.[C:14]1([C:20]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:28]3[C@H:24]([CH2:25][NH:26][CH2:27]3)[S@:23](=[O:29])[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:30]1([C:20]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:28]3[C@H:24]([CH2:25][NH:26][CH2:27]3)[S@:23](=[O:29])[CH2:22][CH2:21]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131719251(1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-mandelate

Product 1

HCID 54345056(1R*,4aR*,7aR*)-(+)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 cm3 of dichloromethane and 7.0 cm3 of 1N aqueous sodium hydroxide are added to 2.06 g of (1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-mandelate. The mixture is stirred for a few minutes after dissolution of the starting product, the organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is disintegrated in an ethyl acetate and ethyl ether mixture, the solid is washed with diisopropyl oxide and dried. 1.14 g of (1R*,4aR*,7aR*)-(-)-4,4-diphenylperhydrothiopyrano-[2,3-c]pyrrole 1-oxide are obtained in the form of a white solid; melting point 192° C. [α]D 20 =-405°, (c=0.46; acetic acid).

Workup

  1. dissolutionafter dissolution of the starting product
  2. dry with materialthe organic phase is dried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. washthe solid is washed with diisopropyl oxide
  5. customdried

Sources & evidence

ORD record
ord-1d5e34ed79d64834990ada365350b32e
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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