Potassium borohydride → HCID 23458657, compound

HRID 1679943Notes

Reaction equation

HRID 1679943 reaction equation
[OH:1][C:2]1([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:6][S:5][C:4](=[S:7])[N:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[BH4-].[K+]>CO.O.C(Cl)(Cl)Cl.C(OCC)(=O)C>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:3][C:4](=[S:7])[S:5][CH2:6][CH:2]([OH:1])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 2

HCID 4192641Potassium borohydrideHCID 23458664HCID 23458664, compound

Product 1

HCID 23458657HCID 23458657, compoundYield 72.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure of Example 3 is followed, but a solution of methyl 3-[4-hydroxy-3-(pyrid-2-yl)-2-thioxothiazolidin-4-yl]-propionate (18.0 g) in methanol (200 cc) and a solution of potassium borohydride (3.25 g) in distilled water (50 cc) are used as the starting materials at a maximum of 5° C. The reaction is allowed to proceed for 2 hours at between 2° and 5° C. The crude product (17.0 g) is dissolved in a mixture of chloroform (80 cc) and ethyl acetate (20 cc). The solution is chromatographed on silica (0.063-0.2 mm) (350 g) contained in a column of diameter 4.2 cm. Elution is carried out with a mixture of chloroform (1,200 cc) and ethyl acetate (300 cc), this eluate being discarded, and then with a mixture of chloroform (2,800 cc) and ethyl acetate (700 cc), this eluate being collected and evaporated under reduced pressure (20 mm Hg) at 45° C. and then dried under reduced pressure (0.2 mm Hg) at 50° C. 2-Hydroxy-4-methoxycarbonylbutyl pyrid-2-yldithiocarbamate (13.2 g) is obtained.

Workup

  1. customare used as the starting materials at a maximum of 5° C
  2. customThe solution is chromatographed on silica (0.063-0.2 mm) (350 g)
  3. washElution
  4. additionis carried out with a mixture of chloroform (1,200 cc) and ethyl acetate (300 cc)
  5. additionwith a mixture of chloroform (2,800 cc) and ethyl acetate (700 cc)
  6. customthis eluate being collected
  7. customevaporated under reduced pressure (20 mm Hg) at 45° C.
  8. customdried under reduced pressure (0.2 mm Hg) at 50° C

Sources & evidence

ORD record
ord-cd527113fe70482eaa2addc88d9c2927
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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