Ethyl Acetate → HCID 90052284, compound

HRID 2284743Notes

Reaction equation

HRID 2284743 reaction equation
[C:1]([C:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH2:8][CH2:9][O:10][CH3:11])[CH2:4][CH2:5][O:6][CH3:7])#[N:2].[BH4-].[Na+].C(OCC)(=O)C.[OH-].[Na+]>CO.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])([CH2:4][CH2:5][O:6][CH3:7])[CH2:8][CH2:9][O:10][CH3:11]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 90052280HCID 90052280, compound

Product 1

HCID 90052284HCID 90052284, compoundYield 141.1%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl (3-cyano-1,5-dimethoxypentan-3-yl)carbamate (G20, 192 mg) and cobalt(II) chloride (183 mg) in methanol (7 mL), sodium borohydride (134 mg) was added at room temperature, and the mixture was stirred at the same temperature for 4 hours. To the reaction mixture, ethyl acetate and 1.0 mol/L aqueous sodium hydroxide were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain tert-butyl (3-(aminomethyl)-1,5-dimethoxypentan-3-yl)carbamate (G21, 275 mg).

Workup

  1. additionwas added at room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8e7e83a21c534976b589ae97422956c4
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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