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

HRID 375480Notes

Reaction equation

HRID 375480 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 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 cm3 of dichloromethane and 30 cm3 of 1N aqueous sodium hydroxide are added to 9.2 g of (1R*,4aR*,7aR*)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (S)-(+)-mandelate. The mixture is stirred for 10 minutes, 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 diisopropyl oxide mixture, the solid is washed with diisopropyl oxide and dried. 5.6 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 198° C. [α]D 20 +434°, (c =0 45; acetic acid).

Workup

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

Sources & evidence

ORD record
ord-99965b118e6c45f4a16a7191605ef0f5
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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