Hydrochloric Acid → HCID 58313095, compound

HRID 535152Notes

Reaction equation

HRID 535152 reaction equation
[C:1]([N:4]1[C:8]2([CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH:5]1[C:14]([O:16]CC)=[O:15])(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>C1COCC1.O.CO>[C:1]([N:4]1[C:8]2([CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH:5]1[C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58313107HCID 58313107, compound

Product 1

HCID 58313095HCID 58313095, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 1-acetyl-8-oxa-1-azaspiro[4.5]decane-2-carboxylate (170) (93 mg, 0.34 mmol) in THF/water/methanol (1.1 mL/0.6 mL/0.6 mL) was added lithium hydroxide monohydrate (29 mg, 0.69 mmol) and the reaction stirred at room temperature for 3 h. The reaction is treated with 1N HCl (0.7 mL) and partitioned between EtOAc and 0.1 N HCl, the aqueous layer was extracted twice with EtOAc, the combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid (79 mg, 95% yield).

Workup

  1. custompartitioned between EtOAc and 0.1 N HCl
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5291da2f63b747fcbbc8eee07a72ed17
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

Loading…