2-Oxa-5-azaspiro[3.4]octane-5-carboxylic acid, 7-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester → 1538626-90-2

HRID 1500927Notes

Reaction equation

HRID 1500927 reaction equation
C(OC([NH:11][CH:12]1[CH2:19][C:15]2([CH2:18][O:17][CH2:16]2)[N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13]1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH:12]1[CH2:19][C:15]2([CH2:16][O:17][CH2:18]2)[N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13]1

Participants

4

Reactant 1

HCID 899238142-Oxa-5-azaspiro[3.4]octane-5-carboxylic acid, 7-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester

Product 1

HCID 899240621538626-90-2Yield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 7-{[(benzyloxy)carbonyl]amino}-2-oxa-5-azaspiro[3.4]octane-5-carboxylate (566 mg, 1.56 mmol) in 20 mL of MeOH was stirred with 10% Pd/C (100 mg) under hydrogen atmosphere at room temperature for 50 minutes. The resulting mixture was filtered and the filtration was concentrated in vacuo to afford tert-butyl 7-amino-2-oxa-5-azaspiro[3.4]octane-5-carboxylate (343 mg, yield: 96.3%) as light viscous oil.

Workup

  1. filtrationThe resulting mixture was filtered
  2. filtrationthe filtration
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-a3dfc268d2894ff79f1608cd6ff1d536
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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