Hydrochloric Acid → 3',4'-dihydro-4'-hydroxy-7'-fluorospiro[imidazolidine-4,1'(2'H)-naphthalene]2,5-dione

HRID 482687Notes

Reaction equation

HRID 482687 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[CH2:7][CH2:8][C:9]32[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[OH:18][CH:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[C:9]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13563112HCID 13563112, compound

Product 1

HCID 135630973',4'-dihydro-4'-hydroxy-7'-fluorospiro[imidazolidine-4,1'(2'H)-naphthalene]2,5-dioneYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 15.5 g. (0.0625 mole) of 3',4'-dihydro-7'-fluorospiro [imidazolidine-4,1'(2'H)-naphthalene]2,4',5-trione in 300 ml. of methanol cooled to 0° C. was added 4.8 g. (0.012 mole) of sodium borohydride over a period of 20 minutes. After stirring for one hour at 0° C. 100 ml. of 10% hydrochloric acid was added and the methanol removed under vacuum. The solid suspension was filtered and the solids dried, 7.3 g. (47% yield).

Workup

  1. additionwas added 4.8 g
  2. customthe methanol removed under vacuum
  3. filtrationThe solid suspension was filtered
  4. customthe solids dried

Sources & evidence

ORD record
ord-bab1ecc67f0a4cb8b7d86cfdc4374ae8
Source dataset
uspto-grants-1986_03
Patent number
US04575507

Reaction notes

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