Hydrochloric Acid → 7a-(3-methyl-5-isoxazolyl)-hexahydro-1H-pyrrolizine hydrochloride

HRID 3284Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[C:5]([C:7]23[CH2:14][CH2:13][CH2:12][N:11]2[CH2:10][CH2:9][CH2:8]3)[O:4][N:3]=1.[ClH:15]>CCOCC>[ClH:15].[CH3:1][C:2]1[CH:6]=[C:5]([C:7]23[CH2:14][CH2:13][CH2:12][N:11]2[CH2:10][CH2:9][CH2:8]3)[O:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7a-(3-methyl-5-isoxazolyl)-hexahydro-1H-pyrrolizine (from step 1e, 189 mg, 0.98 mmol) was immersed in Et2O (7 mL) and cooled to 0° C. A solution of Et2O saturated with HCl (g) was added to the reaction vessel dropwise with stirring. The solvent was carefully removed and the remaining white solid triturated with Et2O (2×) followed by recrystallization out of MeOH/Et2O (126.5 mg, 56%). mp 169°-171° C. MS (CI/NH3) m/e: 193 (M+H)+. 1H NMR (D2O, 300 MHz) δ2.20-2.41 (m, 9H), 2.60-2.68 (m, 2H), 3.31-3.39 (m, 2H), 3.71-3.79 (m, 2H), 6.59 (s, 1H). Anal. Calcd for C11H17ClN2O: C, 57.76; H, 7.49; N, 12.25. Found: C, 57.84; H, 7.34; N, 12.13.

Workup

customThe solvent was carefully removed
customthe remaining white solid triturated with Et2O (2×)
customfollowed by recrystallization out of MeOH/Et2O (126.5 mg, 56%)

Sources & evidence

ORD record: ord-c8ec9bcee30b4b59a1991ab13c706c61
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733912

Reaction notes

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