Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate → 1,4-Dioxa-7-azaspiro[4.4]nonane

HRID 1677841Notes

Reaction equation

HRID 1677841 reaction equation
C(OC([N:11]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[O:14]1[C:13]2([CH2:18][CH2:19][NH:11][CH2:12]2)[O:17][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 15165037Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate

Product 1

HCID 151650391,4-Dioxa-7-azaspiro[4.4]nonaneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-benzyloxycarbonyl-1,4-dioxa-7-azaspiro[4.4]nonane (34.79 g, step iii, no more than 123.7 mmol) and 10% Pd—C (13.9 g) in ethanol (90 mL) was hydrogenolyzed (60 psi) in a Parr shaker apparatus at room temperature for 1.5 hour. The catalyst was filtered off, the solvent was evaporated in vacuo and the residue was pumped under high vacuum for 20 min. to yield 15.86 g of the title compound (yield 99.3%).

Workup

  1. customat room temperature
  2. customfor 1.5 hour
  3. filtrationThe catalyst was filtered off
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-cf45520e353a481e81d63f8041cf29f0
Source dataset
uspto-grants-2011_08
Patent number
US08008342B2

Reaction notes

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