1,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamate → 1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropaneacetic acid

HRID 1430703Notes

Reaction equation

HRID 1430703 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5]1.C(Cl)Cl.[OH2:18].CC#N>O>[C:10]([O:9][C:8]([NH:7][C:4]1([CH2:3][C:2]([OH:18])=[O:1])[CH2:5][CH2:6]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 129931391,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamateHCID 21961003HCID 21961003, compound

Product 1

HCID 215252351-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropaneacetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

RuCl3.H2O (124 mg, 0.6 mmol) was added to a solution of tert-butyl 1-(2-hydroxyethyl)cyclopropylcarbamate (6.1 g, 30 mmol), and NaIO4 (19.0 g, 90 mmol) in DCM/H2O/CH3CN (20 mL/40 mL/20 mL). The mixture was stirred at rt for 3 hrs. The mixture was then diluted with H2O (100 mL), and extracted with DCM (3×). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (0˜30% gradient elution EtOAc/petroleum ether) to afford 2-(1-(tert-butoxycarbonylamino)cyclopropyl)acetic acid (6.0 g, 90%) as a white solid. ESI-MS (EI+, m/z): 238 [M+Na]+.

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (0˜30% gradient elution EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-ae51e3ffebba4318b0854bc4b22bc66a
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

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