Hydrochloric Acid → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-cyclohex-1-en-1-yl)-phenyl]-methanone

HRID 1793998Notes

Reaction equation

HRID 1793998 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=4)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].[H][H].Cl>CO.C(OCC)C>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][CH:25]([OH:29])[CH:24]=4)=[CH:21][CH:22]=3)=[O:16])[CH2:6][C:5]=12

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 101999193-[4-(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-cyclohex-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 10178077(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-cyclohex-1-en-1-yl)-phenyl]-methanoneYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-[4-(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-cyclohex-2-enone of Example 24 (0.100 g, 0.261 mmol) and cerium (III) chloride (0.064 g, 0.261 mmol) were dissolved in methanol (1.3 mL) followed by addition of solid sodium borohydride (0.010 g, 0.261 mmol). After hydrogen evolution ceased (approximately 5 minutes), 0.1 N hydrochloric acid (50 mL) was added and the resulting mixture extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated. A slightly yellow solid was isolated which was dissolved in boiling diethyl ether and filtered. The product was precipitated from the filtrate by addition of pentane and the precipitate filtered and dried to afford the title compound (0.100 g) as an amorphous white solid.

Workup

  1. additionwas added
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customA slightly yellow solid was isolated which
  7. dissolutionwas dissolved
  8. filtrationfiltered
  9. customThe product was precipitated from the filtrate by addition of pentane
  10. filtrationthe precipitate filtered
  11. customdried

Sources & evidence

ORD record
ord-5f36afab113842339506369e8350a84b
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

Loading…