Lithium borohydride → HCID 10299574, compound

HRID 1835310Notes

Reaction equation

HRID 1835310 reaction equation
[BH4-].[Li+].C[O:4][C:5]([C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:10]([C:20](=[O:38])[N:21]([CH2:23][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)[CH3:22])=[CH:9][N:8]=1)=O>C(OCC)C.C1(C)C=CC=CC=1>[F:32][C:30]([F:31])([F:33])[C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([C:34]([F:37])([F:35])[F:36])[CH:27]=1)[CH2:23][N:21]([CH3:22])[C:20](=[O:38])[C:10]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:12][C:7]([CH2:5][OH:4])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 10207712HCID 10207712, compound

Product 1

HCID 10299574HCID 10299574, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 9 mg (4 mmol) lithium borohydride in 0.5 ml diethyl ether was added a solution of 346 mg (0.678 mmol) 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-pyridine-2-carboxylic acid methyl ester in 0.6 ml toluene. The mixture was gradually heated to 100° C., whereby diethyl ether was distilled off. After heating for 2 h at 100° C. the resulting suspension was concentrated. The residue was treated with 5 ml of a 1 M aqueous solution of hydrochloric acid for 5 min. Basification with potassium carbonate was followed by extraction with tert-butyl methyl ether. The combined organic extracts were dried with sodium sulfate and concentrated. Flash chromatography afforded 240 mg (73.4%) of the title compound as a light brown oil.

Workup

  1. distillationwhereby diethyl ether was distilled off
  2. temperatureAfter heating for 2 h at 100° C. the resulting suspension
  3. concentrationwas concentrated
  4. additionThe residue was treated with 5 ml of a 1 M aqueous solution of hydrochloric acid for 5 min
  5. extractionBasification with potassium carbonate was followed by extraction with tert-butyl methyl ether
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c107361c98834c869ff6d2cd0c14562d
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

Loading…