Acetone → HCID 68815972, compound

HRID 734322Notes

Reaction equation

HRID 734322 reaction equation
[CH:1]([N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:19][C:20]([CH3:22])=[O:21].[C:23](O[BH-](OC(=O)C)OC(=O)C)(=[O:25])C.[Na+].[CH2:37](Cl)Cl>>[CH:1]([N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([CH:13]2[CH2:14][CH2:15][N:16]([C:23]([O:21][C:20]([CH3:37])([CH3:22])[CH3:19])=[O:25])[CH2:17][CH2:18]2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11550595AG-H-20408

Product 1

HCID 68815972HCID 68815972, compound

Procedure

The product of D8, Step 2 (2.0 g) was dissolved in DCM (50 ml) and acetone (0.94 ml) added and the mixture stirred for 5 min. Sodium triacetoxyborohydride (2.7 g) was then added and the reaction stirred at rt for 1.5 h. The reaction mixture was then washed with saturated potassium carbonate solution (50 ml), sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml). The organic layer was dried (MgSO4) and evaporated to give the subtitled compound as a white solid (1.50 g).

Workup

  1. stirringthe reaction stirred at rt for 1.5 h
  2. washThe reaction mixture was then washed with saturated potassium carbonate solution (50 ml), sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-4355d4a6639e41e09905cb4ab546c64d
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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