Lithium hydroxide, monohydrate → 1538626-88-8

HRID 1500925Notes

Reaction equation

HRID 1500925 reaction equation
[CH2:1]1[C:4]2([CH2:8][CH:7]([C:9]([O:11]CC)=[O:10])[CH2:6][N:5]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:3][O:2]1.O.[OH-].[Li+]>O.CO>[C:17]([O:16][C:14]([N:5]1[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[CH2:8][C:4]21[CH2:3][O:2][CH2:1]2)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89924107HCID 89924107, compound

Product 1

HCID 899240881538626-88-8Yield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-tert-butyl 7-ethyl 2-oxa-5-azaspiro[3.4]octane-5,7-dicarboxylate (514 mg, 1.80 mmol) and lithium hydroxide monohydrate (378 mg, 9.0 mmol) in 1 mL of H2O and 10 mL of MeOH was stirred at room temperature overnight. The resulting mixture was concentrated in vacuo. The residue was stirred with saturated aqueous solution of 2-hydroxypropane-1,2,3-tricarboxylic acid (15 mL) and then extracted with DCM (15 mL×2). The combined organic layers were dried over Na2SO4 and then concentrated in vacuo to afford 5-(tert-butoxycarbonyl)-2-oxa-5-azaspiro[3.4]octane-7-carboxylic acid (444 mg, yield: 95.9%) as a white solid.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. stirringThe residue was stirred with saturated aqueous solution of 2-hydroxypropane-1,2,3-tricarboxylic acid (15 mL)
  3. extractionextracted with DCM (15 mL×2)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dbe393a591a4a5280c7c17dd76e33ef
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

Loading…