Acetic Acid → 4-Benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylamino]-2-piperazinone

HRID 2086231Notes

Reaction equation

HRID 2086231 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([N:17]=[C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13](=[O:31])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([NH:17][CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]2)[C:13](=[O:31])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 227272314-Benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylideneamino]-2-piperazinone

Product 1

HCID 178253894-Benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylamino]-2-piperazinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The resultant 4-benzyloxycarbonyl-1-{[1-(tert-butoxycarbonyl)-4-piperidinylidene]amino}-2-piperazinone was dissolved in methanol (40 ml), combined with acetic acid (1.2 g) with cooling on ice, followed by sodium cyanoborohydride (943 mg), and then stirred at room temperature for 30 minutes. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate and brine, dried, concentrated and purified by a column chromatography (ethyl acetate) to obtain 4-benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylamino]-2-piperazinone (3.7 g) as a colorless amorphous material.

Workup

  1. temperaturewith cooling on ice
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with aqueous sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by a column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-0ad60b1ebbf64696a84e07106dc5aa8d
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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