Sodium borohydride → HCID 20136112, compound

HRID 579706Notes

Reaction equation

HRID 579706 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[C:18](=[S: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+]>C(O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[C:18](=[S: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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20136114HCID 20136114, compound

Product 1

HCID 20136112HCID 20136112, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

32.9 g (0.10 mol) of 8-(4-chloro-2-fluoro-5-methoxyphenyl)-7-oxo-9-thioxo-1,8-diazabicyclo[4.3.0]nonane were dissolved in 250 ml of ethanol. 5.7 g (0.15 mol) of sodium borohydride were added in portions at a rate such that the temperature was kept at 30° C. When the addition was complete, the mixture was stirred for a further 30 minutes at 30° C. and poured into 600 ml of ice-water. The precipitate was filtered off under suction, dried and recrystallized from methanol. 24.9 g (75% of theory) of 8-(4-chloro-2-fluoro-5-methoxyphenyl)-7-hydroxy-9-thioxo-1,8-diazabicyclo[4.3.0]nonane were obtained in the form of colorless crystals having the melting point 208°-215° C.

Workup

  1. customwas kept at 30° C
  2. additionWhen the addition
  3. filtrationThe precipitate was filtered off under suction
  4. customdried
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a85365e3efad4acbb7b5743eb8625b69
Source dataset
uspto-grants-1988_06
Patent number
US04749403

Reaction notes

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