Methylamine → N-methyl-1,4-dioxaspiro(4.5)decan-8-amine

HRID 1663018Notes

Reaction equation

HRID 1663018 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(Cl)Cl.CN.[C:17]([BH3-])#[N:18].[Na+]>C(O)(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:18][CH3:17])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 6344DichloromethaneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 16786570N-methyl-1,4-dioxaspiro(4.5)decan-8-amineYield 43.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1,4-dioxa-spiro[4.5]decan-8-one (3.1 g, 20 mmol) and CH2Cl2 (50 mL) was stirred with methylamine (15 mL, 30 mmol, 2.0M solution in THF), sodium cyanoborohydride (1.3 g, 20 mmol), and acetic acid (0.1 mL) at room temperature. After 8 hours, the reaction mixture was washed with water (50 mL) and concentrated. The residue was purified by flash chromatography to afford 1.5 g of (1,4-dioxa-spiro[4.5]dec-8-yl)-methyl-amine as an oil.

Workup

  1. washthe reaction mixture was washed with water (50 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4554f1545a354faca8a7824f54180310
Source dataset
uspto-grants-2011_10
Patent number
US08034826B2

Reaction notes

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