Hydroxyamine hydrochloride → 3-Methyl-4,5,6,7-tetrahydro-1-oxa-2,7-diaza-cyclopenta[e]azulene-9-carboxylic acid ethyl ester

HRID 481087Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=[O:23])[CH:21]([C:24](=O)[CH3:25])[CH2:20][CH2:19][CH2:18][C:8]=2[N:9](C(OC(C)(C)C)=O)[CH:10]=1)=[O:5])[CH3:2].Cl.[NH2:28]O>CCO>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22]3[O:23][N:28]=[C:24]([CH3:25])[C:21]=3[CH2:20][CH2:19][CH2:18][C:8]=2[NH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

In a sealed tube were 5-acetyl-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.1 mmol) and hydroxylamine hydrochloride (2.2 mmol) and 10 mL EtOH. The mixture is heated at 100° C. for 16 hours. The solvent is evaporated in vacuo and the residue is taken up in CH2Cl2 and washed two times with NaHCO3 (aq). The organic layer is dried over Na2SO4 and evaporated in vacuo and the residue chromatographed using 10% MeOH in CH2Cl2 as mobile phase to yield 3-methyl-4,5,6,7-tetrahydro-1-oxa-2,7-diaza-cyclopenta[e]azulene-9-carboxylic acid ethyl ester as a white solid (76%). 1H NMR (CDCl3+CD3OD) 1.3 (t, 3H), 1.90-1.98 (m, 2H), 2.10 (s, 3H), 2.35 (t, 2H), 2.75-2.82 (m, 2H), 4.21 (q, 2H), 7.15 (s, 1H)

Workup

customIn a sealed tube were
customThe solvent is evaporated in vacuo
washwashed two times with NaHCO3 (aq)
dry with materialThe organic layer is dried over Na2SO4
customevaporated in vacuo
customthe residue chromatographed

Sources & evidence

ORD record: ord-8e22cab6394949c881a1d5265b7810fa
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653471B2

Reaction notes

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