Isoamyl Nitrite → HCID 86687041, compound

HRID 2282459Notes

Reaction equation

HRID 2282459 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[N:17](OCCC(C)C)=[O:18].CCOC(C)=O>C1COCC1.C1CCCCC1>[C:1]([C:5]1[NH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[C:8]([N:17]=[O:18])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 71168396HCID 71168396, compound

Product 1

HCID 86687041HCID 86687041, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

A yellow solution of Intermediate 51a (390 mg, 1.82 mmol) and isopentyl nitrite (0.294 mL, 2.18 mmol) in THF (10 mL) was stirred at 50° C. for 8 h, then cooled to RT and concentrated in vacuo to leave a dark green oil. FCC, using 0-25% EtOAc in cyclohexane, gave the title compound as a green solid (154 mg, 35%). LCMS (Method 3): Rt 3.82 min, m/z 244 [MH+].

Workup

  1. concentrationconcentrated in vacuo
  2. customto leave a dark green oil

Sources & evidence

ORD record
ord-fabc71650a604b93821b3c8250d823db
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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