Hydrochloric Acid → 5-[(Benzyloxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid

HRID 1185800Notes

Reaction equation

HRID 1185800 reaction equation
C[O:2][C:3]([CH:5]1[CH2:11][C:8]2([CH2:10][CH2:9]2)[CH2:7][N:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:4].[Li+].[OH-].Cl>C1COCC1.CO>[CH2:15]([O:14][C:12]([N:6]1[CH:5]([C:3]([OH:4])=[O:2])[CH2:11][C:8]2([CH2:9][CH2:10]2)[CH2:7]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66620688O5-benzyl O6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate

Product 1

HCID 596105415-[(Benzyloxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Aza-spiro[2.4]heptane-5,6-dicarboxylic acid 5-benzyl ester 6-methyl ester (244 mg, 0.840 mmol) was dissolved in THF (2.0 mL)/MeOH (1.5 mL) An aqueous solution of LiOH (35.5 mg, 0.84 mmol) was added and stirring at room temperature was continued. After 3 hours, the reaction was neutralized with aqueous HCl (1M) and the organic solvents were removed in vacuo. The crude mixture was diluted with water and EtOAc and the organic layer was collected. All volatiles were removed in vacuo and the crude acid was used without further purification. LCMS-ESI+: calc'd for C15H17NO4: 275.3 (M+). Found: 276.3 (M+H+).

Workup

  1. additionwas added
  2. customthe organic solvents were removed in vacuo
  3. additionThe crude mixture was diluted with water and EtOAc
  4. customthe organic layer was collected
  5. customAll volatiles were removed in vacuo
  6. customthe crude acid was used without further purification

Sources & evidence

ORD record
ord-2c42117f84d3437faae7ab1423793fd8
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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