Borane → HCID 10297313, compound

HRID 900776Notes

Reaction equation

HRID 900776 reaction equation
[CH3:1][O:2][C@@:3]1([C:11]#[C:12][C:13]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[OH:14])[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1.B.[H-].[Na+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>C1COCC1>[CH3:1][O:2][C@@:3]1([C:11]#[C:12][C:13]([O:14][CH2:29][C:30]([O:32][CH3:33])=[O:31])([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

6

Reactant 4

HCID 6331BoraneHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10109130HCID 10109130, compound

Product 1

HCID 10297313HCID 10297313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1,1-di(2-thienyl)-2-propyn-1-ol compound complexed with borane 193 (200 mg, 0.54 mmol) in THF (10 ml) under nitrogen and at room temperature was treated with NaH (60% dispersion in oil, 23 mg, 0.59 mmol). After 20 minutes, methyl bromoacetate (55 μL, 0.59 mmol) was added in one portion. After 16 hours, the reaction was quenched with water, and the mixture was then diluted with AcOEt. The organic phase was washed with brine, dried over MgSO4 and evaporated to dryness to afford the methyl {[3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1,1-di(2-thienyl)-2-propynyl]oxy}acetate compound complexed with borane (1:1) 194 as an oil (130 mg, 55%). This compound was used without other purification in the next step.

Workup

  1. waitAfter 16 hours
  2. customthe reaction was quenched with water
  3. additionthe mixture was then diluted with AcOEt
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-96d1f52abdff411187c2c910e0e32b60
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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