Methyl iodide → (1R,4S)-methyl 4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylate

HRID 270537Notes

Reaction equation

HRID 270537 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@H:12]([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@H:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7019281(1R,4S)-(+)-4-(Boc-amino)-2-cyclopentene-1-carboxylic acid

Product 1

HCID 10610130(1R,4S)-methyl 4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylateYield 103.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (10.0 g, 44 mmol) in DMF (25 mL) was added potassium carbonate (6.33 g, 45.8 mmol) followed by methyl iodide (4.0 mL, 64 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with EtOAc. The solution was washed with water four times and brine one time, dried (MgSO4) and concentrated. The residue was dried under high vacuum overnight to provide the title compound (11 g, 99%). MS calculated for C12H19NO4: (M+H)+ 242; found 142.1 (M-Boc+H)+. 1H NMR (CDCl3) δ 5.86 (m, 2H), 4.90 (m, 1H), 4.80 (m, 1H), 3.72 (s, 3H), 3.50 (m, 1H), 2.51 (m, 1H), 1.86 (m, 1H), 1.42 (s, 9H).

Workup

  1. washThe solution was washed with water four times and brine one time
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was dried under high vacuum overnight

Sources & evidence

ORD record
ord-0bb0488a437a48e5a911a7a18b10d991
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

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