Acetaldehyde → HCID 58859680, compound

HRID 1786013Notes

Reaction equation

HRID 1786013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:37])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:25][CH:24]=3)[C@@H:14]([CH3:38])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH:39](=O)[CH3:40].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:37])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]4[CH2:36][CH2:35][N:34]([CH2:39][CH3:40])[CH2:33][CH2:32]4)=[CH:25][CH:24]=3)[C@@H:14]([CH3:38])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68926408HCID 68926408, compound

Product 1

HCID 58859680HCID 58859680, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The piperdine was reacted with acetaldehyde, Na(OAc)3BH in dichloromethane at room temperature overnight. Then washed with 1N NaOH, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (10% methanol/90% dichloromethane) to afford the product (55%).

Workup

  1. washThen washed with 1N NaOH
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down
  5. customThe crude residue was purified by silica gel chromatography (10% methanol/90% dichloromethane)

Sources & evidence

ORD record
ord-217d6172dd4a4309820f436cdcba0e57
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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