Sodium Hydroxide → 1-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

HRID 1748612Notes

Reaction equation

HRID 1748612 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.Cl.[CH3:13][NH2:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.C(O)(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:13][NH2:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 109539781-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamineYield 100.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dioxaspiro[4,5]decan-8-one (10.0 g) and acetic acid (4.4 ml) in dichloromethane (128 ml) were added methylamine hydrochloride (5.19 g) and sodium triacetoxyborohydride (16.3 g), and stirred at room temperature for 2.5 hours. After completion of the reaction, 4 N aqueous solution of sodium hydroxide (90 ml) was added thereto, and extracted with dichloromethane. The organic layer was dried over sodium sulfate, and then the solvent was evaporated to give (1,4-dioxaspiro[4,5]dec-8-yl)methylamine as an orange oil (11.0 g).

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-03ef24141f7d43a9a5617f5967b6b0a0
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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