Isoamyl Nitrite → HCID 54492934, compound

HRID 1755643Notes

Reaction equation

HRID 1755643 reaction equation
[CH:1]1([N:7]([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:20][CH2:21][CH3:22])[C:12](=[O:23])[CH2:11][N:10]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[N:30](OCCC(C)C)=[O:31]>C1(C)C=CC=CC=1>[CH:1]1([N:7]([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:20][CH2:21][CH3:22])[C:12](=[O:23])[C:11](=[N:30][OH:31])[N:10]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 19961906HCID 19961906, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54492934HCID 54492934, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

The product from step (A) (5 g, 0.016 mol) was dissolved in dry toluene (500 ml) and cooled to -20° C. under an atmosphere of nitrogen. Potassium t-butoxide (8.59 g, 0.080 mol) was added followed after 30 minutes by the dropwise addition of isoamyl nitrite (2.36 ml, 0.0176 mol). The reaction mixture was stirred at -20° C. for 18 hours. The reaction was quenched by the addition of water (50 ml) and the mixture was neutralized to pH 7.4 by the addition of 1M hydrochloric acid. The solvents were removed in vacuo, the resulting solid was resuspended in dichloromethane and absorbed onto silica. The product was purified using flash silica chromatography, eluting with 0.5% 0.88 ammonium solution/2% methanol/dichloromethane followed by chromatography on an alumina column, eluting with 2% methanol/dichloromethane followed by 5% methanol/dichloromethane. Yield--2.31 g (42%) as a pale yellow foam. 1H NMR (DMSO)δ0.52-2.06 (16 H, m), 2.60-2.92 (3H, m), 3.60 (1H, m), 4.26 (1H, m), 7.22-7.66 (14H, m), 9.84 and 10.02 (1H, 2×s).

Workup

  1. customThe reaction was quenched by the addition of water (50 ml)
  2. additionthe mixture was neutralized to pH 7.4 by the addition of 1M hydrochloric acid
  3. customThe solvents were removed in vacuo
  4. customabsorbed onto silica
  5. customThe product was purified
  6. washeluting with 0.5% 0.88 ammonium solution/2% methanol/dichloromethane
  7. washeluting with 2% methanol/dichloromethane
  8. customYield--2.31 g (42%) as a pale yellow foam

Sources & evidence

ORD record
ord-557e2d9b05144113ab873e182675ba1f
Source dataset
uspto-grants-1995_08
Patent number
US05438055

Reaction notes

Loading…