4-Pentenal → HCID 68862216, compound

HRID 898879Notes

Reaction equation

HRID 898879 reaction equation
[C:1]([O:5][C:6](=[O:21])[C:7]([S:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([NH2:20])[CH2:14]2)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:22](=O)[CH2:23][CH2:24][CH:25]=[CH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[C:7]([CH3:9])([S:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([NH:20][CH2:26][CH2:25][CH2:24][CH:23]=[CH2:22])[CH2:14]2)[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 164184-PentenalHCID 5049666Sodium triacetoxyborohydrideHCID 68860578HCID 68860578, compound

Product 1

HCID 68862216HCID 68862216, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-(2-aminoindan-5-ylsulfanyl)-2-methylpropionic acid tert-butyl ester (0.220 g; 0.72 mmol), dissolved in DCE (4 mL), is added pent-4-enal (0.060 mg; 0.72 mmol) followed by sodium triacetoxyborohydride (0.21 g; 1.0 mmol) and the reaction mixture stirred for 18 h at RT. The reaction mixture was diluted with CH2Cl2, washed with H2O, brine, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure to afford 2-methyl-2-(2-pent-4-enylaminoindan-5-ylsulfanyl)propionic acid tert-butyl ester as a crude oil.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2067570c72e141f79a7b16f55262b159
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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