Sodium borohydride → HCID 13914899, compound

HRID 364354Notes

Reaction equation

HRID 364354 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[CH2:19][C:20]([NH2:22])=[O:21].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[CH:8]2[OH:12])=[CH:4][C:3]=1[CH2:19][C:20]([NH2:22])=[O:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 13030807HCID 13030807, compound

Product 1

HCID 13914899HCID 13914899, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)acetamide (6.8 g., 0.02 mole) in ethanol (100 ml) is added sodium borohydride (760 mg. 0.02 mole). After one hour another portion of sodium borohydride (760 mg, 0.021 mole) is added and stirring continued for 3 hours. The reaction mixture is poured into ice water and extracted with ethyl acetate. The ethyl acetate extract is washed with water and dried over magnesium sulfate. The ethyl acetate is evaporated at reduced pressure to give (6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-hydroxy-2-methyl-1H-inden-5-yl)acetamide consisting of a mixture of two diastereomer, each of which is a racemate.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washis washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe ethyl acetate is evaporated at reduced pressure

Sources & evidence

ORD record
ord-a54696ae5f984acbb2bb1ba4ba581a7b
Source dataset
uspto-grants-1986_08
Patent number
US04604403

Reaction notes

Loading…