Triethylamine → 1-Tert-butoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane

HRID 1457972Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH:16]2[C:13]([C:18]([OH:20])=[O:19])([CH2:14][CH2:15]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](N(CC)CC)C.C1(P(N=[N+]=[N-])([C:36]2[CH:41]=[CH:40]C=CC=2)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C)(C)C>[C:41]([O:19][C:18]([C:13]12[CH2:14][CH2:15][CH:16]1[CH2:17][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:12]2)=[O:20])([CH3:40])([CH3:36])[CH3:21]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane-1-carboxylic acid (2.90mmol) in tertiary butanol (15 ml) were added 0.53 ml (3.8 mmol) of triethylamine and 0.819 ml (3.8 mmol) of diphenylphosphorylazide, followed by 9 hours of stirring at 70° C. After cooling to room temperature, the reaction solution was poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 817.8 mg (2.27 mmol, 78.3% for 2 steps from Reference Example B-2) of the title compound.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customAfter evaporation of the solvent
customthe resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-22da75820c18456dac71ceb04cf9c4cf
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849757

Reaction notes

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