Cinnamaldehyde → HCID 10456106, compound

HRID 706355Notes

Reaction equation

HRID 706355 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([N:17]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:19]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:18]2)=[O:16])[CH:12]=[CH:11][N:10]=1.[CH:31](=O)/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1.C(O)C>[Cl:8][C:9]1[CH:14]=[C:13]([C:15]([N:17]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:19]3([CH2:20][CH2:21][N:22]([CH2:31]/[CH:32]=[CH:33]/[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:23][CH2:24]3)[CH2:18]2)=[O:16])[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 637511CinnamaldehydeHCID 86605018HCID 86605018, compound

Product 1

HCID 10456106HCID 10456106, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Chloropyridin-4-yl)carbonylspiro[indoline-3,4′-piperidine]trifluoroacetic acid salt (0.44 g) and trans-cinnamaldehyde (0.29 g) were suspended in tetrahydrofuran (8 ml) and ethanol (6 ml). Borane-pyridine complex (0.26 ml) was added and the reaction stirred vigorously overnight at room temperature. The mixture was evaporated and partitioned between dichloromethane and water. The organics were dried over anhydrous magnesium sulfate and evaporated in vacuo. Flash chromatography [SiO2; ethyl acetate-hexane-triethylamine (25:75:1), increasing polarity to (50:50:1)] yielded 0.42 g (94%) of the desired product.

Workup

  1. additionBorane-pyridine complex (0.26 ml) was added
  2. customThe mixture was evaporated
  3. custompartitioned between dichloromethane and water
  4. dry with materialThe organics were dried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. temperatureFlash chromatography [SiO2; ethyl acetate-hexane-triethylamine (25:75:1), increasing polarity to (50:50:1)]

Sources & evidence

ORD record
ord-6b2c3c616d5046d88dac6a5f436f22f1
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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