Trimethylsilyldiazomethane → Methyl 3-amino-3-cyclobutylpropanoate

HRID 2171853Notes

Reaction equation

HRID 2171853 reaction equation
[NH2:1][CH:2]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([OH:6])=[O:5].[N+](=[CH:13][Si](C)(C)C)=[N-]>CO.C1C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[NH2:1][CH:2]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([O:6][CH3:13])=[O:5]

Participants

7

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 247302513-Amino-3-cyclobutylpropanoic acid2×

Product 1

HCID 73425272Methyl 3-amino-3-cyclobutylpropanoateYield 95%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of racemic 3-amino-3-cyclobutyl-propanoic acid, 48a, (0.34 g, 2.38 mmol) in MeOH (10.2 mL) and benzene (10.2 mL) was added diazomethyltrimethyl-silane (3.56 mL of 2 M solution, 7.13 mmol) and the reaction mixture was allowed to stir at room temperature under a nitrogen atmosphere overnight. The mixture was diluted with EtOAc and brine. The layers were separated and the organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 354 mg (95%) of crude product that was used without further purification: 1H NMR (400 MHz, CDCl3) δ 3.71-3.66 (m, 3H), 3.18-2.98 (m, 1H), 2.46-2.32 (m, 2H), 2.27-1.63 (m, 10H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fbe25dadfa4454a879c104628e750fb
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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