Formaldehyde → HCID 59730361, compound

HRID 130728Notes

Reaction equation

HRID 130728 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1.[CH2:25]=O.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:17]=[C:16]([CH2:18][N:19]([CH3:25])[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 9979717HCID 9979717, compound

Product 1

HCID 59730361HCID 59730361, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 227 (1.0 equiv) in MeOH (0.2 M solution) was treated with formaldehyde (5 equiv) and stirred at room temperature (r.t.) for 2 hours. Sodium Borohydride was added and stirred at r.t. overnight. The solvent was removed under vacuum and crude residue was purified by silica gel chromatography using the appropriate eluent (typically mixtures CHCl3/EtOH 7%/NH4OH 0.7%) to afford the title compound as a solid.

Workup

  1. stirringstirred at r.t. overnight
  2. customThe solvent was removed under vacuum and crude residue
  3. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-312ef97f372548adb7bde3eb3b05d7bd
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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