Acetaldehyde → HCID 18437122, compound

HRID 242589Notes

Reaction equation

HRID 242589 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:23](=O)[CH3:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:14]([CH2:23][CH3:24])[CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 42880079HCID 42880079, compound

Product 1

HCID 18437122HCID 18437122, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(4-Chloro-benzylamino)-piperidine-1-carboxylic acid tert-butyl ester was dissolved in CH2Cl2 and acetaldehyde (0.678 g, 3.2 mmol), Na(OAc)3BH (0.163 g, 3.7 mmol) and 1 drop of AcOH was added. The solution was stirred in a sealed vessel for 10 h. The reaction mixture was washed with 1N NaOH, brine and dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (15% ethyl acetate/85% hexane) to yield the title compound (0.350 g, 40%).

Workup

  1. washThe reaction mixture was washed with 1N NaOH, brine
  2. dry with materialdried over Mg2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. custompurified by Biotage flash chromatography (15% ethyl acetate/85% hexane)

Sources & evidence

ORD record
ord-fe445b144952457e9b1642d32548af12
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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