(1S,2R)-(+)-Norephedrine → HCID 3627260, compound

HRID 1729265Notes

Reaction equation

HRID 1729265 reaction equation
[CH3:1][CH:2]([NH2:11])[CH:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].[C:14](=[S:16])=[S:15]>>[CH3:1][CH:2]1[CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[S:16][C:14](=[S:15])[NH:11]1.[CH3:1][CH:2]1[CH:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:10][C:14](=[S:15])[NH:11]1

Participants

5

Reactant 3

HCID 4786(1S,2R)-(+)-NorephedrineHCID 6348Carbon DisulfideHCID 14798Sodium Hydroxide

Product 2

HCID 3627260HCID 3627260, compoundHCID 12697701HCID 12697701, compound

Procedure

Carbon disulphide (27 ml) was added to a mixture of (1S, 2R )-(+)-norephedrine (5.0 g) and aqueous sodium hydroxide (50 ml of 15% solution) and the mixture stirred for 24 hours. Excess carbon disulphide was evaporated under reduced pressure and the residue poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and evaporated. The residue was chromatographed on silica gel (eluent-ether/hexane; 1:1) to give 4-methyl-5-phenylthiazolidine-2-thione and 4-methyl-5-phenyloxazolidine-2-thione. A solution of the first of these thiones (0.80 g) in dimethylformamide was treated with sodium hydride (0.12 g of 80% dispersion in oil). When hydrogen evolution had ceased, intermediate A (1.2 g) was added, over one hour, and the mixture allowed to stand for 60 hours. The mixture was poured into water and extracted with ether. The extract was worked up in conventional manner to give methyl (E)-2-[2-[[(4-methyl-5-phenylthiazol-2-in-2-yl)thio]methyl]phenyl]-3-methoxy-2-propenoate, as a gum. (Compound 1).

Workup

  1. customExcess carbon disulphide was evaporated under reduced pressure
  2. additionthe residue poured into water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (eluent-ether/hexane; 1:1)

Sources & evidence

ORD record
ord-8aad9b1ef56a4c87ad35e1d30f5fa38e
Source dataset
uspto-grants-1994_07
Patent number
US05332752

Reaction notes

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