Acetone → HCID 52939884, compound

HRID 1614898Notes

Reaction equation

HRID 1614898 reaction equation
[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[O:15])[C:7]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.[BH4-].[Na+].CC(C)=O.ClCCl>C(O)C>[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[OH:15])[C:7]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:6]=3[CH2:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 52939883HCID 52939883, compound

Product 1

HCID 52939884HCID 52939884, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-cyclopropyl-1-(2-(4-fluorophenyl)-2-oxoethyl)-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (65.0 mg, 0.170 mmol) from Example 5 in ethanol (1 ml) was added sodium borohydride (6.4 mg, 0.170 mmol) and the reaction mixture was stirred at room temperature over weekend. Then was added acetone (0.062 ml) followed by dilution with dichloromethane. The resulting solution was washed with water and the organic phase was dried over sodium sulfate and filtered. Evaporation gave the desired product (30 mg, 46%).

Workup

  1. washThe resulting solution was washed with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customEvaporation

Sources & evidence

ORD record
ord-e803529905e74d3794b9fc2f21ac6749
Source dataset
uspto-grants-2014_07
Patent number
US08765728B2

Reaction notes

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