Triethylamine → HCID 59159287, compound

HRID 1096255Notes

Reaction equation

HRID 1096255 reaction equation
[CH3:1][CH:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[CH:9]=2)[CH2:6][CH2:5][N:4]([CH2:19][CH2:20][CH:21]=O)[C:3]1=[O:23].Cl.[CH2:25]1[C:27]2([CH2:32][CH2:31][NH:30][CH2:29][C@H:28]2[OH:33])[CH2:26]1.C(N(CC)CC)C>CCO.C(Cl)Cl.N1C=CC=CC=1>[OH:33][C@@H:28]1[CH2:29][N:30]([CH2:21][CH2:20][CH2:19][N:4]2[CH2:5][CH2:6][N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[CH:9]=3)[CH:2]([CH3:1])[C:3]2=[O:23])[CH2:31][CH2:32][C:27]21[CH2:26][CH2:25]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2×HCID 866383913-[3-Methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionaldehyde

Product 1

HCID 59159287HCID 59159287, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionaldehyde (117 mg, 0.35 mmol) in EtOH (1.6 mL) and CH2Cl2 (1.6 mL) were added (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2; 70 mg, 0.43 mmol) triethylamine (43 mg, 0.43 mmol), borane pyridine complex solution (8 M in pyridine, 0.093 mL, 0.74 mmol), then after 1 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2, then CH2Cl2/MeOH 4:1) afforded the title compound (90 mg, 58%). Light yellow oil, MS: 442.3 (M+H)+.

Workup

  1. customafter 1 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cab87d80541046e8a5cffb219910810f
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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