Methylamine → HCID 118390114, compound

HRID 1478017Notes

Reaction equation

HRID 1478017 reaction equation
O=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.CN.[BH3-][C:23]#[N:24].[Na+]>CCO>[CH3:23][NH:24][CH:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 118390114HCID 118390114, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (2.15 g, 8.05 mmol) in EtOH (20 mL) was added 33% methanamine in EtOH (3.7 g, 40.3 mmol), and the mixture was stirred at r.t for 1.5 h. Then NaBH3CN (1.5 g, 24.2 mmol) was added to the mixture. After that the resulting mixture was stirred at r.t overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as brown oil (1.05 g, 46.2%).

Workup

  1. stirringAfter that the resulting mixture was stirred at r.t overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record
ord-374889012e5a4580a53e174f214dfd50
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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