Water → HCID 20136110, compound

HRID 579705Notes

Reaction equation

HRID 579705 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[C:18](=[O:19])[N:17]3[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[C:18](=[O:19])[N:17]3[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[CH:11]2[OH:20])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 13175257HCID 13175257, compound

Product 1

HCID 20136110HCID 20136110, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

31.3 g (0.10 mol) of 8-(4-chloro-2-fluoro-5-methoxyphenyl)-7,9-dioxo-1,8-diazabicyclo[4.3.0]nonane were dissolved in 200 ml of methanol. 5.7 g (0.15 mol) of sodium borohydride were added in portions at a rate such that the temperature was kept at 30°-40° C. When the addition was complete, the mixture was stirred for a further 1 hour at 30° C. and poured into 500 ml of water. The precipitate which deposited was filtered off under suction and dried. 29.8 g (94% of theory) of 8-(4-chloro-2-fluoro-5-methoxyphenyl)-7-hydroxy-9-oxo-1,8-diazabicyclo[4.3.0]nonane were obtained in the form of colorless crystals having the melting point 155°-157° C.

Workup

  1. customwas kept at 30°-40° C
  2. additionWhen the addition
  3. filtrationThe precipitate which deposited was filtered off under suction
  4. customdried

Sources & evidence

ORD record
ord-3ee41df7db5e4e8ea4f9f3f698c1af22
Source dataset
uspto-grants-1988_06
Patent number
US04749403

Reaction notes

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