Triethylamine → HCID 86668859, compound

HRID 331090Notes

Reaction equation

HRID 331090 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]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 86668860HCID 86668860, compound

Product 1

HCID 86668859HCID 86668859, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. washthe resulting mixture was washed with 1N hydrogen chloride (1 mL), water (2 mL), brine (2 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a92ddfc04a9e4a2a897385c1e3b49a38
Source dataset
uspto-grants-2014_11
Patent number
US08877749B2

Reaction notes

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