Cerium(III) chloride → Racemic (10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

HRID 2053741Notes

Reaction equation

HRID 2053741 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])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[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])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:6][C:5]=12

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 102950443-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methyl-phenyl]-2-methyl-cyclohex-2-enone

Product 1

HCID 10273123Racemic (10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanoneYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methyl-phenyl]-2-methyl-cyclohex-2-enone of Example 8 (0.350 g, 0.853 mmol), and cerium (III) chloride (0.210 g, 0.853 mmol) were combined in methanol (4.3 mL) followed by addition of sodium borohydride (0.032 g, 0.853 mmol). The reaction was stirred at room temperature until gas evolution ceased (approximately 2 minutes), then quenched with 0.1 N hydrochloric acid (100 mL), causing a white precipitate to form. The precipitate was filtered and purified by flash column chromatography on silica gel eluting with 50% ethyl acetate in hexane to afford 0.310 g of the title alcohol as a white solid.

Workup

  1. custom(approximately 2 minutes)
  2. customquenched with 0.1 N hydrochloric acid (100 mL)
  3. customto form
  4. filtrationThe precipitate was filtered
  5. custompurified by flash column chromatography on silica gel eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e313688a07b74a49af0afced1e805e14
Source dataset
uspto-grants-2008_02
Patent number
US07326700B2

Reaction notes

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