Lithium hydroxide, monohydrate → HCID 71187300, compound

HRID 712790Notes

Reaction equation

HRID 712790 reaction equation
[CH3:1][C:2]1([C:17]([O:19]C)=[O:18])[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:7][C:4]2([CH2:6][CH2:5]2)[CH2:3]1.O[Li].O>O1CCOCC1.O>[C:13]([O:12][C:10]([N:9]1[CH2:8][CH2:7][C:4]2([CH2:5][CH2:6]2)[CH2:3][C:2]1([CH3:1])[C:17]([OH:19])=[O:18])=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71186642HCID 71186642, compound

Product 1

HCID 71187300HCID 71187300, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

6-tert-butyl 5-methyl 5-methyl-6-azaspiro[2.5]octane-5,6-dicarboxylate (D5) (320 mg, 1.13 mmol) was partitioned between dioxane/water (8/8 ml) prior addition of LiOH H2O (190 mg, 4.52 mmol). The mixture was stirred at RT for 18 hrs then heated at 150° C. under microwave irradiation 40 min (4 cycles of 10 min each). Organic solvent was evaporated off and the aqueous solution washed with EtOAc (2×10 ml), acidified to pH˜4 with citric acid sat. sol. and extracted with EtOAc (3×10 ml). The organic phases were washed with NaCl sat. sol, dried over Na2SO4 and evaporated to reduced pressure to afford the title compound (D6) (114 mg).

Workup

  1. temperaturethen heated at 150° C. under microwave irradiation 40 min (4 cycles of 10 min each)
  2. customOrganic solvent was evaporated off
  3. washthe aqueous solution washed with EtOAc (2×10 ml)
  4. extractionextracted with EtOAc (3×10 ml)
  5. washThe organic phases were washed with NaCl sat. sol
  6. dry with materialdried over Na2SO4
  7. customevaporated to reduced pressure

Sources & evidence

ORD record
ord-bffa82e3c3404c76b4a6e72d3c98d0c6
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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