Trifluoroacetic acid → 8-Benzoyl-2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one

HRID 215946Notes

Reaction equation

HRID 215946 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]1([N:16]2[CH2:20][CH2:19][C:18]3([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:17]2=[O:26])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)C(C)C)(C)C.C(O)(C(F)(F)F)=O>CN(C)C=O.CO>[C:1]([N:23]1[CH2:24][CH2:25][C:18]2([C:17](=[O:26])[N:16]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:20][CH2:19]2)[CH2:21][CH2:22]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 588931652-Cyclohexyl-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 167394408-Benzoyl-2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Benzoyl chloride (15 μL, 0.00013 mol) was added to a solution of 2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one (20.0 mg, 0.0000846 mol) and N,N-diisopropylethylamine (44 μL, 0.00025 mol) in N,N-dimethylformamide (1.0 mL). The mixture was stirred at room temperature for 30 min, then adjusted to be acidic (pH to −2.0) with TFA, and diluted with methanol (0.8 mL). The resulting solution was purified by Prep-HPLC to give 8-benzoyl-2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one. LCMS: (M+H)+=341.20.

Workup

  1. customThe resulting solution was purified by Prep-HPLC

Sources & evidence

ORD record
ord-6a753242a42a4b5e8b8de5f5799253a4
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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