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

HRID 1053494Notes

Reaction equation

HRID 1053494 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 603 (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 (1 M) 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 606 was used without further purification. LCMS-ESI+: calc'd for C15H17NO4: 275.3 (M+). Found: 276.3 (M+H+).

Workup

  1. customthe organic solvents were removed in vacuo
  2. additionThe crude mixture was diluted with water and EtOAc
  3. customthe organic layer was collected
  4. customAll volatiles were removed in vacuo
  5. customthe crude acid 606 was used without further purification

Sources & evidence

ORD record
ord-b9e4fe76d9df4274816e7400a3a614dd
Source dataset
uspto-grants-2016_07
Patent number
US09393256B2

Reaction notes

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