Hydrochloric Acid → HCID 21566091, compound

HRID 1580337Notes

Reaction equation

HRID 1580337 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH:14]([S:15][CH2:16][C:17]([OH:26])(C)[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:13]([OH:27])[CH2:12][C:11]1=[O:28])([OH:3])=[O:2].[BH4-].[Na+].Cl>CO.O>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH:14]([S:15][CH2:16][CH:17]([OH:26])[C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH:13]([OH:27])[CH2:12][C:11]1=[O:28])([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21565919HCID 21565919, compound

Product 1

HCID 21566091HCID 21566091, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

2 g of 2-(6-carboxyhexyl)-3-(2-hydroxy-2-methyl-2-p-tolylethylthio)-4-hydroxy-cyclopentanone is dissolved in 50 ml methanol, two drops of water are added and with cooling by ice and agitating 1.5 g NaBH4 is added during 2 hours. After addition of 50 ml ice-water the mixture is acidified with aqueous HCl and extracted three times with respectively 50 ml portions of dimethylether. The combined organic phases are washed three times with a saturated aqueous NaCl-solution, dried over Na2SO4, filtered and evaporated. After chromatographic purification of the residue (silica gel/chloroform : methanol = 9 : 1) 2-(6-carboxyhexyl-3-(2-hydroxy-2-methyl-2-p-tolylethylthio)-1,4-cyclopentanediol is obtained as an oil,

Workup

  1. temperaturewith cooling by ice
  2. additionis added during 2 hours
  3. extractionextracted three times with respectively 50 ml portions of dimethylether
  4. washThe combined organic phases are washed three times with a saturated aqueous NaCl-solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customAfter chromatographic purification of the residue (silica gel/chloroform : methanol = 9 : 1) 2-(6-carboxyhexyl-3-(2-hydroxy-2-methyl-2-p-tolylethylthio)-1,4-cyclopentanediol
  9. customis obtained as an oil

Sources & evidence

ORD record
ord-33da3ae4f87e4cf5b73dc6193e1ebea2
Source dataset
uspto-grants-1976_01
Patent number
US03932487

Reaction notes

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