Dimethylformamide → HCID 19106897, compound

HRID 1197484Notes

Reaction equation

HRID 1197484 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH:8]=1.[N+:20]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(C(OC(C)(C)C)=O)=[N-:21].[Cl-].[NH4+].CN(C)[CH:40]=[O:41]>>[C:2]([O:4][C:40]([N:21]([C:13]1([C:9]2[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[NH:20][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[O:41])([CH3:5])([CH3:3])[CH3:1]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 109760102-(Pyrid-3-yl)cyclohexanoneHCID 19106893Di-t-butyl diazodicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19106897HCID 19106897, compound

Conditions

Temperature
20 °C

Procedure

Potassium t-butoxide (3.7 g, 33 mmol) was added, in one portion, to a stirred solution of 2-(pyrid-3-yl)cyclohexanone (5.3 g, 30 mmol) in dimethylformamide (60 ml) at 0° C. After 60 minutes the dark red solution was treated with di-t-butyl diazodicarboxylate (7.6 g, 33 mmol) over 5 minutes. The mixture was then allowed to warm to 20° C. over 1 hour, poured into saturated ammonium chloride solution (50 ml) and extracted with ethyl acetate (2×25 ml). The combined organic extracts were successively washed with water (20 ml) and saturated brine (20 ml) and dried over sodium sulphate. Concentration in vacuo gave the crude product which was recrystallised from petroleum ether (60°-80° C.; 150 ml) to give 2-(N,N'-di-t-butoxycarbonylhydrazino)-2-(pyrid-3-yl)cyclohexanone (7.1 g, 17.5 mmol), m.p. 123°-125° C.;

Workup

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. washThe combined organic extracts were successively washed with water (20 ml) and saturated brine (20 ml)
  3. dry with materialdried over sodium sulphate
  4. concentrationConcentration in vacuo
  5. customgave the crude product which
  6. customwas recrystallised from petroleum ether (60°-80° C.; 150 ml)

Sources & evidence

ORD record
ord-78a762870ee1455c8af616941c81c009
Source dataset
uspto-grants-1994_01
Patent number
US05276046

Reaction notes

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