Sodium borohydride → HCID 21538620, compound

HRID 1076891Notes

Reaction equation

HRID 1076891 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:7]1([CH2:11][C:10](=[O:12])[NH:9][CH2:8]1)[CH2:6][C:5]2=[O:16].[BH4-].[Na+]>CO.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:7]1([CH2:11][C:10](=[O:12])[NH:9][CH2:8]1)[CH2:6][CH:5]2[OH:16]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 21538654HCID 21538654, compound

Product 1

HCID 21538620HCID 21538620, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

210 g of 5-chlorospiro[indane-1,3'-pyrrolidine]-3,5'-dione are dissolved in 2,5 liters of methanol, and a solution of 20 g of sodium borohydride in 250 cc of water and 5 cc of caustic soda solution is added at room temperature at such a rate that the temperature in the reaction vessel does not exceed 25°. The solution is stirred at room temperature for 2 hours, is then poured on ice and extracted several times with chloroform. The 5-chloro-3 -hydroxyspiro[indane-1,3'-pyrrolidin]-5'-one, obtained after concentrating the chloroform solution by evaporation, is a mixture of diastereoisomers, having a M.P. of 155°-180°, and containing approximately equal parts of the 1RS,3SR and the 1RS,3RS isomer. Pure (1RS,3SR)-5-chloro-3-hydroxyspiro[indane-1,3'-pyrrolidin]-5'-one, having a M.P. of 213°-216°, may be obtained by extracting repeatedly with chloroform and subsequently recrytallizing twice from methanol.

Workup

  1. customdoes not exceed 25°
  2. additionis then poured on ice
  3. extractionextracted several times with chloroform

Sources & evidence

ORD record
ord-5396ac89c2214e83aae8a234d2ae46cc
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

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