Diisopropylethylamine → HCID 11976243, compound

HRID 1013342Notes

Reaction equation

HRID 1013342 reaction equation
[C:1]1([C:7]2[CH2:11][C:10]3([CH2:16][CH2:15][CH:14]([C:17](O)=[O:18])[CH2:13][CH2:12]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:62][C:63]1[C:64]([N:69]2[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]2)=[N:65][CH:66]=[CH:67][CH:68]=1>C1COCC1>[Cl:62][C:63]1[C:64]([N:69]2[CH2:70][CH2:71][N:72]([C:17]([CH:14]3[CH2:13][CH2:12][C:10]4([O:9][N:8]=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH2:11]4)[CH2:16][CH2:15]3)=[O:18])[CH2:73][CH2:74]2)=[N:65][CH:66]=[CH:67][CH:68]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 114129441-(3-Chloropyridin-2-yl)piperazineHCID 579514503-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid

Product 1

HCID 11976243HCID 11976243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid (750 mg, 2.9 mmol) was slowly added to a solution of N-ethyldiisopropylamine (1.02 g, 7.1 mmol), 1-hydroxybenzotriazole hydrate (320 mg, 2.4 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (758 mg, 2.4 mmol) and 1-(3-chloropyridin-2-yl)piperazine (467 mg, 2.4 mmol) in abs. THF (17 ml). The reaction mixture was stirred overnight and the solvent removed under vacuum. The residue was taken up in EtOAc (100 ml). The precipitate formed was removed by suction-filtration. The organic phase was washed successively with sat. aq. NaCl solution, sat. aq. NaHCO3 solution, sat. aq. ammonium sulphate solution and sat. aq. NaCl solution, dried over magnesium sulphate and the solvent removed under vacuum. The precipitate and the residue were purified by column chromatography (silica gel, hexane/EtOAc 1:1). The desired product [4-(3-chloropyridin-2-yl)piperazin-1-yl]-(3-phenyl-1-oxa-2-azaspiro[4.5]dec-2-en-8-yl)methanone was obtained as a cis isomer (294 mg, 24% of the theoretical amount) and trans isomer (192 mg, 15% of the theoretical amount).

Workup

  1. customthe solvent removed under vacuum
  2. customThe precipitate formed
  3. customwas removed by suction-filtration
  4. washThe organic phase was washed successively with sat. aq. NaCl solution, sat. aq. NaHCO3 solution, sat. aq. ammonium sulphate solution and sat. aq. NaCl solution
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under vacuum
  7. customThe precipitate and the residue were purified by column chromatography (silica gel, hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-6d0ee1de9230445fbb0d626e169420f5
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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