Ethyl Acetate → tert-Butyl [4-(aminomethyl)oxan-4-yl]carbamate

HRID 2284737Notes

Reaction equation

HRID 2284737 reaction equation
[C:1]([C:3]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].[BH4-].[Na+].C(OCC)(=O)C.[OH-].[Na+]>CO.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 21112788HCID 21112788, compound

Product 1

HCID 71744123tert-Butyl [4-(aminomethyl)oxan-4-yl]carbamateYield 91.2%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalyst2×HCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl (4-cyanotetrahydro-2H-pyran-4-yl)carbamate (G14, 210 mg) and cobalt(II) chloride (241 mg) in methanol (9 mL), sodium borohydride (175 mg) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, cobalt(II) chloride (241 mg) and sodium borohydride (175 mg) were added at room temperature, and the mixture was stirred at the same temperature for 2 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 (4-(aminomethyl)tetrahydro-2H-pyran-4-yl)carbamate (G15, 195 mg).

Workup

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

Sources & evidence

ORD record
ord-8a2661df79e6456481f6287c9856a3fa
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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