Acetic Acid → HCID 69545831, compound

HRID 2086254Notes

Reaction equation

HRID 2086254 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:19][CH2:20]2)[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 69545990(3S)-3-(tert-butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidone

Product 1

HCID 69545831HCID 69545831, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S)-3-(tert-Butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidone (3.57 g) was dissolved in methanol (40 ml), combined with acetic acid (2.05 g) with cooling on ice, followed by sodium cyanoborohydride (807 mg) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated, and the residue was combined with an aqueous solution of sodium hydroxide, extracted with dichloromethane, dried, concentrated, and purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (2.56 g) as a colorless amorphous material.

Workup

  1. temperaturewith cooling on ice
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. custompurified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record
ord-813ac87904194d809ac3afa2643898db
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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