Potassium sodium tartarate → HCID 21265967, compound

HRID 566284Notes

Reaction equation

HRID 566284 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([C:19](OC)=[O:20])=[C:13]([C:15](OC)=[O:16])[N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:6]=2[CH:30]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:19][OH:20])=[C:13]([CH2:15][OH:16])[N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:6]=2[CH:30]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 21266009HCID 21266009, compound

Product 1

HCID 21265967HCID 21265967, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.29 g of dimethyl 8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-1,2-dicarboxylate in 100 ml of tetrahydrofuran was cooled to −78° C. and20 ml of a 1M lithium aluminium hydride solution in tetrahydrofuran was added dropwise in a manner such that the temperature did not exceed −70° C. After completion of the addition the mixture was brought slowly to room temperature and stirred for 1 h. Then, it was treated dropwise with saturated sodium potassium tartrate solution and stirred well for 12 h. The insoluble material was filtered off, the filtrate was concentrated and the residue was recrystallized from isopropanol. The concentrated mother liquor was purified by chromatography on 300 g of silica gel with dichloromethane/methanol/glacial acetic acid 90:10:2 and the fractions containing the product, after removal of the solvent, were again recrystallized from isopropanol. There were thus isolated a total of 4.1 g (65%) of [8-chloro-6-(2-fluorophenyl)-2-hydroxymethyl-4H-imidazo[1,2-a]-[1,4]benzodiazepin-1-yl]-methanol of m.p. 222° C.

Workup

  1. additionwas added dropwise in a manner such that the temperature
  2. customdid not exceed −70° C
  3. additionAfter completion of the addition the mixture
  4. customwas brought slowly to room temperature
  5. stirringstirred well for 12 h
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated
  8. customthe residue was recrystallized from isopropanol
  9. customThe concentrated mother liquor was purified by chromatography on 300 g of silica gel with dichloromethane/methanol/glacial acetic acid 90:10:2
  10. additionthe fractions containing the product
  11. customafter removal of the solvent
  12. customwere again recrystallized from isopropanol

Sources & evidence

ORD record
ord-43806dcb994749dd8d66b5d8be415e47
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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