Hydrochloric Acid → HCID 54033174, compound

HRID 867536Notes

Reaction equation

HRID 867536 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]3[CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](OCC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl.O>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]3[CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH2:16][OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 54398902HCID 54398902, compound

Product 1

HCID 54033174HCID 54033174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 13.3 g (40 mmol) of ethyl (S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate in 85 ml of tetrahydrofuran is heated to 50° and a suspension of 1.06 g (48.7 mmol) of lithium borohydride in 15 ml of tetrahydrofuran is then added dropwise to the solution obtained. The white suspension is subsequently heated to boiling under reflux for 70 minutes. The mixture is cooled to 20° and 54 ml of a solution consisting of 27 ml of conc. hydrochloric acid and 27 ml of water is added dropwise thereto. The tetrahydrofuran is distilled off in vacuo and the aqueous residue is made alkaline with 25 percent ammonia. The mixture is left to crystallize in an ice-bath for 1 hour, the precipitated material is filtered off under suction, rinsed with water and dried at 80° in a high vacuum. There is obtained (S)-8-chloro-12,12 a-dihydro-1-(hydroxymethyl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of decomposition point 256°-258°.

Workup

  1. temperatureis heated to 50°
  2. additionis then added dropwise to the solution
  3. customobtained
  4. temperatureThe white suspension is subsequently heated
  5. temperatureunder reflux for 70 minutes
  6. temperatureThe mixture is cooled to 20°
  7. additionis added dropwise
  8. distillationThe tetrahydrofuran is distilled off in vacuo
  9. waitThe mixture is left
  10. customto crystallize in an ice-bath for 1 hour
  11. filtrationthe precipitated material is filtered off under suction
  12. washrinsed with water
  13. customdried at 80° in a high vacuum

Sources & evidence

ORD record
ord-21925184847e4dd982f3895fa3747b91
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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