Ammonium Chloride → HCID 12859194, compound

HRID 1156975Notes

Reaction equation

[C:1]([CH:5]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH:10]2[N:6]1[CH2:7][CH2:8][CH2:9]2)(OC)=[O:2].[Cl-].[Mg+2].[Cl-].[CH3:22][Mg]Br.[Cl-].[NH4+]>C1COCC1.CCOCC>[C:1]([CH:5]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH:10]2[N:6]1[CH2:7][CH2:8][CH2:9]2)(=[O:2])[CH3:22]

Participants

Conditions

Temperature: -70 °C

Procedure

In 7 ml of THF, was dissolved 295 mg of 2-carbomethoxy-3-phenyl-1,3-diazabicyclo[3,3,0]octane. After addition of 138 mg of anhydrous magnesium chloride, the mixture was refluxed for 10 minutes. To the mixture cooled to -70° C., was added dropwise an ether solution of 1.36 equivalents of methylmagnesium bromide. After having been stirred for 15 minutes at -70° C., the reaction mixture was admixed with saturated aqueous ammonium chloride solution and ether and brought to room temperature. The mixture was extracted with ether and the ether layer was dried. The ether layer was freed from the solvent by distillation in vacuo and the residue was purified by alumina column chromatography to obtain 199 mg (72%) of 2-acetyl-3-phenyl-1,3-diazabicyclo[3,3,0]octane. NMR peaks: δ (ppm)=1.5-2.2 (4H, multiplet), 1.9 (3H, singlet), 2.4-3.3 (3H, multiplet), 3.5-3.9 (2H, multiplet), 4.1 (1H, singlet), 6.1-7.1 (5H, multiplet).

Workup

temperaturethe mixture was refluxed for 10 minutes
custombrought to room temperature
extractionThe mixture was extracted with ether
dry with materialthe ether layer was dried
distillationThe ether layer was freed from the solvent by distillation in vacuo
customthe residue was purified by alumina column chromatography

Sources & evidence

ORD record: ord-62a8c4f12f5a4b519713ddaec9cbf7d9
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04337346

Reaction notes

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