Acetic Acid → HCID 118105524, compound

HRID 2200384Notes

Reaction equation

HRID 2200384 reaction equation
O=[C:2]1[CH2:6][CH2:5][C@H:4]([C:7]([NH:9][C:10]2[CH2:17][CH2:16][C:13]3([CH2:15][CH2:14]3)[CH2:12][C:11]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:8])[CH2:3]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[F:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:35][CH2:34][N:33]([C@@H:2]3[CH2:6][CH2:5][C@H:4]([C:7]([NH:9][C:10]4[CH2:17][CH2:16][C:13]5([CH2:15][CH2:14]5)[CH2:12][C:11]=4[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:8])[CH2:3]3)[CH2:32][CH2:31]2)=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 752601-(4-Fluorophenyl)piperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118119372HCID 118119372, compound

Product 1

HCID 118105524HCID 118105524, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (S)-ethyl 6-(3-oxocyclopentanecarboxamido)spiro[2.5]oct-5-ene-5-carboxylate (0.7 g, 2.23 mmol) in 1,2-dichloroethane (10 ml) were added 1-(4-fluorophenyl)piperazine (0.43 g, 2.40 mmol), glacial acetic acid (0.14 g, 2.40 mmol) and sodium triacetoxy borohydride (0.7 g, 3.44 mmol). The mixture was stirred at RT for 24 h before removal of the solvent. The residue was treated with saturated sodium bicarbonate, extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude residue which was purified by column chromatography over silica gel using ethyl acetate in hexane as eluents to obtain a diastereomeric mixture (7:3) of title compound (0.9 g, 84%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude residue which
  7. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-00f28658b3324f6fb605915371b1ec24
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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