Dimethylformamide → methyl (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate

HRID 1662042Notes

Reaction equation

HRID 1662042 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]N(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].CI>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1268163(1S,2R)-2-(tert-Butoxycarbonylamino)cyclopentanecarboxylic acid

Product 1

HCID 11322482methyl (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (0.88 g) and DMF (8.0 ml) were added cesium carbonate (2.5 g) and methyl iodide (0.82 g) under ice-cooling, followed by stirring at room temperature for 1.5 hours. To the reaction mixture ethyl acetate and water under ice-cooling were added. The organic layer was separated, the aqueous layer was extracted with ethyl acetate (15 ml), and the organic layer was combined and washed with a 10% aqueous citric acid solution, a saturated sodium bicarbonate solution, water, and saturated brine in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain methyl (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate (0.85 g).

Workup

  1. temperaturecooling
  2. additionwere added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (15 ml)
  5. washwashed with a 10% aqueous citric acid solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82c1eec8dd9d4bc5989d5ae1abf11802
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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