Sodium cyanoborohydride → HCID 58696296, compound

HRID 1178329Notes

Reaction equation

HRID 1178329 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)([CH:13]=O)[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].CN.CO.[C:28]([BH3-])#[N:29].[Na+]>CO>[C:1]([O:5][C:6](=[O:23])[N:7]([C:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)([CH2:13][NH:29][CH3:28])[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 57454252Monomethylamine methanolHCID 58696299HCID 58696299, compound

Product 1

HCID 58696296HCID 58696296, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl[1-(3,4-dichlorophenyl)-1-formyl-3-butenyl]methylcarbamate (35 g) was dissolved in methanol (350 mL), and 40% methylamine-methanol solution (44 mL) was added thereto, followed by refluxing for 15 hours. The reaction mixture was cooled to room temperature, and sodium cyanoborohydride (12.5 g) was added thereto, followed by refluxing for 7 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (sequentially through use of n-hexane:ethyl acetate=2:1 and chloroform:methanol=10:1 to 5:1), to thereby give the title compound (24.8 g, 70%).

Workup

  1. temperatureby refluxing for 15 hours
  2. temperatureby refluxing for 7 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified through silica gel column chromatography (sequentially through use of n-hexane

Sources & evidence

ORD record
ord-e3ac1334fed04780a8b93acf6f2bee5e
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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