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

HRID 500048Notes

Reaction equation

HRID 500048 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-1006cd42bd294e36b00d70e9a9eab108
Source dataset
uspto-grants-2010_08
Patent number
US07767830B2

Reaction notes

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