Sodium borohydride → HCID 21986305, compound

HRID 9641Notes

Reaction equation

HRID 9641 reaction equation
C([Li])CCC.[H-].C([Al+]CC(C)C)C(C)C.C(N(C)[C:21]([C:23]1[S:24][CH:25]=[C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[C:27]=1[CH3:28])=[O:22])(C)(C)C.[BH4-].[Na+]>C1CCCCC1.O1CCCC1.C(O)C>[CH3:28][C:27]1[C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=2)=[CH:25][S:24][C:23]=1[CH2:21][OH:22]

Participants

8

Reactant 4

HCID 4311764Sodium borohydrideHCID 21225700DiisobutylaluminumhydrideHCID 21986416N-(tert-butyl)-N,3-dimethyl-4-[4-(trifluoromethyl)phenyl]thiophene-2-carboxamide2×HCID 178418339Butyllithium

Product 1

HCID 21986305HCID 21986305, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

n-Butyllithium (1.6M in hexanes, 1.1 ml) was added dropwise to a mixture of 1M diisobutylaluminium hydride in cyclohexane (1.77 ml) and tetrahydrofuran at 0° C. under nitrogen. This mixture was allowed to stir for 30 minutes then was added to a cooled (0° C.) solution of N-(tert-butyl)-N,3-dimethyl-4-[4-(trifluoromethyl)phenyl]thiophene-2-carboxamide (intermediate 40, 0.210 g) in tetrahydrofuran (2.5 ml) under nitrogen. After 1.5 hours, a solution of sodium borohydride (0.68 g) in ethanol (5 ml) was added and the reaction was allowed to warm to room temperature. After 2 hours, the reaction was quenched with wet tetrahydrofuran then 2M aqueous hydrochloric acid was added and the mixture was stirred for 15 minutes. Ether was added and the water layer removed. The aqueous was extracted with 2 further portions of ether then the combined organic solution was washed with brine then dried (MgSO4) and concentrated. The crude product was purified by SPE (silica cartdrige) using cyclohexane:ethyl acetate (3:1) as eluent to furnish the title compound as a colourless oil.

Workup

  1. additionthen was added to
  2. waitAfter 1.5 hours
  3. waitAfter 2 hours
  4. customthe reaction was quenched with wet tetrahydrofuran
  5. addition2M aqueous hydrochloric acid was added
  6. stirringthe mixture was stirred for 15 minutes
  7. additionEther was added
  8. customthe water layer removed
  9. extractionThe aqueous was extracted with 2 further portions of ether
  10. washthe combined organic solution was washed with brine
  11. dry with materialthen dried (MgSO4)
  12. concentrationconcentrated
  13. customThe crude product was purified by SPE (silica cartdrige)

Sources & evidence

ORD record
ord-92cfef5e59a94c4ba5258e0e370a3505
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Reaction notes

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