Triethylamine → HCID 86668859, compound
Reaction equation
[NH2:1][C:2]1([CH2:17][CH2:18][NH2:19])[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.C(N(CC)CC)C.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:28]=[C:27]1[NH:19][CH2:18][CH2:17][C:2]2([CH2:3][C@H:4]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:5][CH2:6]2)[NH:1]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (1R)-benzyl 3-amino-3-(2-aminoethyl)cyclopentanecarboxylate (from step D, 30 mg, 0.114 mmol) in toluene (2 mL) was added triethylamine (0.048 mL, 0.343 mmol) and 1,1′-Carbonyldiimidazole (37.1 mg, 0.229 mmol). The resulting mixture was stirred at 80° C. for 2 hours. To the reaction mixture was added ethyl acetate (10 mL) and the resulting mixture was washed with 1N hydrogen chloride (1 mL), water (2 mL), brine (2 mL), dried over Na2SO4 and concentrated under reduced pressure to yield (2R)-benzyl 7-oxo-6,8-diazaspiro[4.5]decane-2-carboxylate (20 mg, 0.069 mmol, 60.7% yield) as an oil. It was used as such for the subsequent step without further purification. MS (ESI+) m/z 288 M+
Workup
- washthe resulting mixture was washed with 1N hydrogen chloride (1 mL), water (2 mL), brine (2 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fb8fb56c698b4ff3896507f63ba5a91e
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221819B2
Reaction notes
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