Hydrochloric Acid → 6-[(tert-butoxy)carbonyl]-6-azaspiro[2.5]octane-5-carboxylic acid

HRID 712787Notes

Reaction equation

HRID 712787 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][CH:9]1[C:16]([O-:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([NH2+]C(C1C=CC=CC=1)C)C1C=CC=CC=1.Cl.[Na+].[Cl-]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:12][CH2:13]2)[CH2:10][CH:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 89350970HCID 89350970, compound

Product 1

HCID 711873446-[(tert-butoxy)carbonyl]-6-azaspiro[2.5]octane-5-carboxylic acidYield 81.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-benzyl-1-phenylethanaminium 6-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-5-carboxylate (single unknown enantiomer) (D2) (10 g, 24 mmol) in EtOAc (100 mL) stirred at 0° C. was slowly added aqueous HCl 0.5N (100 ml) saturated with NaCl. After addition was completed, dissolution was observed. The organic layer was decanted, washed with saturated NaCl, dried (Na2SO4) and evaporated in vacuo to afford 5 g of acid which was recrystallized from petroleum ether/EtOAc (60 ml/20 ml) to afford the tile compound (D3) (2.8 g) as white solid.

Workup

  1. additionAfter addition
  2. dissolutiondissolution
  3. customThe organic layer was decanted
  4. washwashed with saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-86ce547e21c143ecabd0b449ec26e602
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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