Lithium borohydride → HCID 10134004, compound

HRID 719195Notes

Reaction equation

HRID 719195 reaction equation
C[O:2][C:3]([C:5]1[C:10]2=[CH:11][CH:12]=[C:13]3[C:22]([N:21]=[C:20]4[C:15]([CH:16]=[CH:17][CH:18]=[C:19]4[C:23](=[O:30])[NH:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[N:14]3)=[C:9]2[CH:8]=[CH:7][CH:6]=1)=O.[BH4-].[Li+]>O1CCCC1.CC(O)C>[CH3:28][N:27]([CH3:29])[CH2:26][CH2:25][NH:24][C:23]([C:19]1[C:20]2[C:15](=[N:14][C:13]3[C:22]([N:21]=2)=[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:3][OH:2])[C:10]2=[CH:11][CH:12]=3)[CH:16]=[CH:17][CH:18]=1)=[O:30]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 11825587HCID 11825587, compound

Product 1

HCID 10134004HCID 10134004, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11-(2-dimethylamino-ethylcarbamoyl)-benzo[a]phenazine-4-carboxylic acid methyl ester (317 mg) in tetrahydrofuran (18 mL) and 2-propanol (10 mL) at 0° C. was added lithium borohydride (2.0M solution in tetrahydrofuran, 1.97 mL) The reaction mixture was stirred at room temperature overnight, and then quenched with ammonium chloride solution. The reaction mixture was extracted with ethyl acetate, dried (MgSO4) and concentrated in vacuo. The residue was purified using flash chromatography (10% MeOH in dichloromethane) to yield the title compound as a yellow solid (98 mg).

Workup

  1. customquenched with ammonium chloride solution
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-e906df01baae4427bc1919cd6b1d5ff9
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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