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

HRID 1698388Notes

Reaction equation

HRID 1698388 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>CCO.[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]nonane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1d (34.8 g, no more than 124 mmol) and 10% Pd—C (14 g) in EtOH (90 mL) was hydrogenolyzed (60 psi) in a Parr shaker apparatus at room temperature for 1.5 h. The catalyst was filtered off, the solvent was evaporated in vacuo and the residue was pumped under high vacuum for 20 min to yield 1e (15.9 g, quant. yield). Rf 0.14 (EtOAc-iPrNH2, 95:5, v/v); 1H NMR (200 MHz, CDCl3) δ 4.00 (s, 4H), 3.10 (t, J 7 Hz, 2H), 2.90 (s, 2H), 2.00 (t, J 7 Hz, 2H); 13C NMR (50 MHz, APT, CDCl3) δ 64.5 (+), 55.0 (+), 45.5 (+), 37.0 (+); IR (film) 3292 cm−1.

Workup

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

Sources & evidence

ORD record
ord-f67a625f61744023a783ddbaeb982faa
Source dataset
uspto-grants-2012_04
Patent number
US08163938B2

Reaction notes

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