Water → 1,8-Dioxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid

HRID 1518144Notes

Reaction equation

HRID 1518144 reaction equation
C([O:3][C:4]([C:6]1[CH2:10][C:9]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[O:8][N:7]=1)=[O:5])C.O.[Li+].[OH-]>CO>[O:8]1[C:9]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 50994112Ethyl 1,8-dioxa-2-azaspiro[4.5]dec-2-ene-3-carboxylate

Product 1

HCID 509941151,8-Dioxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,8-dioxa-2-aza-spiro[4.5]dec-2-ene-3-carboxylic acid ethyl ester (3.00 g, 1.41 mmol, as prepared in the previous step) in MeOH (60 mL) and water (20 mL) was treated with LiOH (649 mg, 1.55 mmol) at rt for 2.5 h. MeOH was removed in vacuo. The resulting aqueous solution was acidified with 1 N aq HCl and extracted three times with EtOAc (100 mL, 100 mL, 50 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to afford the title compound (2.50 g, 96%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 3.86-3.95 (m, 2H), 3.74 (dt, J=11.8, 4.7 Hz, 2H), 3.01 (s, 2H), 1.91-1.99 (m, 2H), 1.80-1.89 (m, 2H).

Workup

  1. customMeOH was removed in vacuo
  2. extractionextracted three times with EtOAc (100 mL, 100 mL, 50 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ccb2b72a5b94afdb1a68d1df3e4fc42
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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