Lithiumtriethylborohydride → HCID 58066680, compound

HRID 390414Notes

Reaction equation

HRID 390414 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:5]=1[CH2:17][S:18][C:19]([CH3:22])([CH3:21])[CH3:20].C([BH-](CC)CC)C.[Li+]>C1COCC1>[C:19]([S:18][CH2:17][C:5]1[CH:6]=[C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=[CH:9][C:4]=1[CH2:3][OH:2])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 23664628Lithiumtriethylborohydride3×HCID 66683310HCID 66683310, compound

Product 1

HCID 58066680HCID 58066680, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-tert-butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-benzoic acid methyl ester (3.83 g, 10.9 mmol) in THF (100 mL) at −10° C. was added lithium triethylborohydride (1M in THF; 24 mL, 24.0 mmol) slowly via syringe. The reaction was allowed to warm to room temperature and stirred for 45 minutes. Analytical LCMS indicated that starting material still remained, so the mixture was cooled to 0° C., and additional lithium triethylborohydride (1M in THF; 12 mL, 12.0 mmol) was added. The reaction was warmed to room temperature, but analytical LCMS indicated that starting material still remained. The mixture was cooled to 0° C. and additional lithium triethylborohydride (1M in THF; 5 mL, 5.0 mmol) was added. The reaction was stirred at room temperature for 1.5 hours, and then the mixture was worked-up and purified to give the title compound.

Workup

  1. temperaturewas cooled to 0° C.
  2. temperatureThe reaction was warmed to room temperature
  3. temperatureThe mixture was cooled to 0° C.
  4. stirringThe reaction was stirred at room temperature for 1.5 hours
  5. custompurified

Sources & evidence

ORD record
ord-0fe2f4e0ca2644b9b4553bfeff403620
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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