(8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester → 8-Methyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 2235219Notes

Reaction equation

HRID 2235219 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:21])[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[CH3:21][C:11]1([NH2:10])[CH2:20][CH2:19][C:14]2([O:15][CH2:16][CH2:17][O:18]2)[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 68468511(8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester

Product 1

HCID 211341968-Methyl-1,4-dioxaspiro[4.5]decan-8-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve (8-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester (13.12 g, 43.0 mmol) in MeOH (400 mL). Exchange air with nitrogen for three times and then add Pd—C (1.0 g, 10%). Exchange the nitrogen with H2 for three times. Stir the reaction mixture under H2 for over night then remove the Pd—C by filtration. Remove the solvent under reduced pressure to give 7.36 g (100%) of the crude 8-Methyl-1,4-dioxa-spiro[4.5]dec-8-ylamine as a colorless oil.

Workup

  1. customthen remove the Pd—C
  2. filtrationby filtration
  3. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-d2ec176f524a4b6ea2756522371949f8
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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