1,4-Dioxane → 1779637-50-1

HRID 712800Notes

Reaction equation

HRID 712800 reaction equation
[CH:1]12[CH2:7][CH:6]1[CH2:5][CH2:4][C@H:3]([C:8]([O:10]CC)=[O:9])[N:2]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O1CCOCC1.O[Li].O>O>[C:16]([O:15][C:13]([N:2]1[CH:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH:6]2[CH:1]1[CH2:7]2)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrate2×HCID 117966693HCID 117966693, compound

Product 1

HCID 780242131779637-50-1Yield 39.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(3R)-2-tert-butyl 3-ethyl 2-azabicyclo[4.1.0]heptane-2,3-dicarboxylate (D21) (600 mg, 2.22 mmol) was partitioned between dioxane (10 ml) and water (5 ml) prior addition of LiOH H2O (370 mg, 8.9 mmol). The mixture was stirred at RT for 18 hrs. Water (10 ml) and LiOH H2O (740 mg, 18 mmol) were added and the mixture left at RT for 66 h. Dioxane was evaporated off and remaining aqueous was washed with Et2O (3×20 ml). Aqueous solution was acidified with acetic acid up to pH 4 and extracted with EtOAc (3×30 ml). Collected organics were washed with NaCl sat., dried over Na2SO4 and evaporated in vacuo to afford the title compound (D22) (210 mg).

Workup

  1. waitthe mixture left at RT for 66 h
  2. customDioxane was evaporated off
  3. washremaining aqueous was washed with Et2O (3×20 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. washCollected organics were washed with NaCl sat.
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-bbd641ace1814f339d5ddcf3cf7fc5c5
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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