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

HRID 1793983Notes

Reaction equation

HRID 1793983 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])[C:24]=4[CH3:30])=[CH:19][C:18]=3[Cl:31])=[O:16])[CH2:6][C:5]=12.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].Cl>CO.CCOCC>[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][CH:25]([OH:29])[C:24]=4[CH3:30])=[CH:19][C:18]=3[Cl:31])=[O:16])[CH2:6][C:5]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 10203009(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(2-methyl-3-oxo-cyclohex-1-en-1-yl)-phenyl]-methanone

Product 1

HCID 10181266(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-phenyl]-methanoneYield 83.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(2-methyl-3-oxo-cyclohex-1-en-1-yl)-phenyl]-methanone of Example 13 (0.060 g, 0.139 mmol) and cerium(III) chloride (0.034 g, 0.139 mmol) were dissolved in methanol (0.7 mL) followed by addition of solid sodium borohydride (0.0053 g, 0.139 mmol). Gas was vigorously evolved from the reaction mixture for approximately two minutes, after which 0.1 N hydrochloric acid (25 mL) was added. A white precipitate formed which was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, concentrated and the residue purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate in hexane. A clear oil was isolated which was dissolved in ether and precipitated with pentane to afford the title compound (0.050 g) as a white solid.

Workup

  1. customA white precipitate formed which
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash column chromatography on silica gel
  6. washeluting with 50% ethyl acetate in hexane
  7. customA clear oil was isolated which
  8. customprecipitated with pentane

Sources & evidence

ORD record
ord-87698a4815354576bafb296597875f12
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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