Water → (1-Aminocyclobut-1-yl)acetic acid, N-BOC protected

HRID 896908Notes

Reaction equation

HRID 896908 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([N:10]1[C:13]2([CH2:16][CH2:15][CH2:14]2)[CH2:12][C:11]1=[O:17])=[O:9])([CH3:6])([CH3:5])[CH3:4].C([O:20]CC)C.O>O1CCCC1>[C:3]([O:7][C:8]([NH:10][C:13]1([CH2:12][C:11]([OH:17])=[O:20])[CH2:16][CH2:15][CH2:14]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 10608554Tert-butyl 2-oxo-1-azaspiro[3.3]heptane-1-carboxylate

Product 1

HCID 10751878(1-Aminocyclobut-1-yl)acetic acid, N-BOC protected

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An 1 N aqueous solution of lithium hydroxide (227 ml, 227 mmol) was added to a solution of 2-oxo-1-azaspiro[3.3]heptane-1-carboxylic acid tert-butylester (48 g, 0.227 mmol) in tetrahydrofuran (200 ml). The reaction mixture was stirred for 2 h. Diethyl ether (200 ml) and water (200 ml) were added. The mixture was stirred for 16 h. The organic layer was isolated. The aqueous phase was extracted with diethyl ether (200 ml). The aqueous phase was acidified with a 10% aqueous solution of sodium hydrogen sulfate until pH 3. The formed precipitation was filtered off, washed with water, and dried in vacuo, to give 38.84 g of (1-(tert-butoxycarbonylamino)cyclobutyl)acetic acid.

Workup

  1. stirringThe mixture was stirred for 16 h
  2. customThe organic layer was isolated
  3. extractionThe aqueous phase was extracted with diethyl ether (200 ml)
  4. customThe formed precipitation
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-70d70275243e4ab794d96cfb295abfb2
Source dataset
uspto-grants-2005_07
Patent number
US06919315B1

Reaction notes

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