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

HRID 1193361Notes

Reaction equation

HRID 1193361 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.CC(O)=O.CN.Cl.[BH3-][C:20]#[N:21].[Na+]>CO>[CH3:20][NH:21][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 16786570N-methyl-1,4-dioxaspiro(4.5)decan-8-amineYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (10.0 g, 64.10 mmol, 1.0 eq.) was dissolved in MeOH (100 ml); AcOH (0.1 ml) and CH3NH2.HCl (8.65 g, 128.21 mmol, 2.0 eq.) were added and stirring was carried out for 2 hours at RT. NaCNBH3 (10.0 g, 160.256 mmol, 2.5 eq.) was added in portions at 0° C. and the mixture was then stirred for 16 hours at RT. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography (Alox, 5% MeOH in DCM). Yield: 54% (6.0 g, 35.08 mmol)

Workup

  1. stirringthe mixture was then stirred for 16 hours at RT
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography (Alox, 5% MeOH in DCM)

Sources & evidence

ORD record
ord-e8580db861c049cbabd5460faa7f719a
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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