Trimethylsilyldiazomethane → HCID 57208391, compound

HRID 1276505Notes

Reaction equation

HRID 1276505 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([C:11]([OH:13])=[O:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:24]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([C:11]([O:13][CH3:24])=[O:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 22116092HCID 22116092, compound

Product 1

HCID 57208391HCID 57208391, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 153 mg of 1-(t-butoxycarbonyl)-4-phenyl-1,2,5,6-tetrahydronicotinic acid in 1 mL of THF and 1 mL of MeOH was added 0.6 mL of TMSCHN2 (2M in hexanes). The reaction was stirred at room temperature for 2 h and concentrated under vacuum. The residue was purified by flash chromatography eluting with 20% EtOAc in hexanes to provide 116 mg of the title compound: 1H NMR (300 MHz, CDCl3): δ1.5 (s, 9H), 2.5-2.6 (m, 2H), 3.5 (s, 3H), 3.6 (t, 2H), 4.2-4.3 (m, 2H), 7.1-7.2 (m, 2H), 7.2-7.4 (m, 3H). RF : 0.68 (50% EtOAc in hexanes).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by flash chromatography
  3. washeluting with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-f5839b87b95c4d8cab13fa2897582723
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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