Acetone → HCID 86596877, compound

HRID 1374318Notes

Reaction equation

HRID 1374318 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]2=[O:24])[C@H:4]([CH:25]([OH:28])[CH2:26][CH3:27])[CH2:3]1.[CH3:29][C:30]([CH3:32])=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>CO>[OH:28][CH:25]([C@@H:4]1[CH2:3][C@H:2]([N:1]([CH:30]([CH3:32])[CH3:29])[CH3:33])[CH2:7][CH2:6][C@@H:5]1[N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:9]1=[O:24])[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 180AcetoneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 86596878HCID 86596878, compound

Product 1

HCID 86596877HCID 86596877, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl (S)-1-((1S,2R,4R)-4-amino-2-(1-hydroxypropyl)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (0.86 mmol) in MeOH (5 mL) was added acetone (0.6 mL), and the mixture was stirred for 10 minutes. Then sodium triacetoxyborohydride (544 mg, 2.58 mmol) was added, and the mixture was stirred for 4 h at rt. At the end of the stirring 37% aq. HCHO (0.4 mL) was added, and the mixture was stirred for 30 min at rt. Finally additional sodium triacetoxyborohydride (181 mg, 0.86 mmol) was added, and the mixture was stirred for 18 h at rt. The reaction was quenched by addition of sat. Na2CO3, and the product was extracted with EtOAc (3×). The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification of the residue via flash chromatography on silica gel with elution by 1:9:90 cNH4OH-MeOH—CH2Cl2 afforded the desired benzyl (S)-1-((1S,2R,4R)-2-(1-hydroxypropyl)-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (267 mg) as an oil.

Workup

  1. stirringthe mixture was stirred for 4 h at rt
  2. stirringthe mixture was stirred for 30 min at rt
  3. stirringthe mixture was stirred for 18 h at rt
  4. customThe reaction was quenched by addition of sat. Na2CO3
  5. extractionthe product was extracted with EtOAc (3×)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue via flash chromatography on silica gel
  11. washwith elution by 1:9:90 cNH4OH-MeOH—CH2Cl2

Sources & evidence

ORD record
ord-dc431bc7b635410e83f2b6358e10b763
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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