Methyl iodide → tert-Butyl [(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]carbamate

HRID 222183

Reaction equation

HRID 222183 reaction equation
[OH:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[O-2].[Ba+2].[OH-].[Ba+2].[OH-].I[CH3:25]>CN(C=O)C>[CH3:25][O:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6093286Barium hydroxideHCID 9855530Barium Oxide Nanoparticle DispersionHCID 17998891tert-Butyl ((1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)carbamate

Product 1

HCID 86614253tert-Butyl [(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]carbamateYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl [(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-carbamate (680 mg, 2.73 mmol), DMF (21.1 mL), barium monoxide (5.02 g, 32.7 mmol), barium hydroxide (2.80 g, 16.4 mmol) and iodomethane (1.70 mL, 27.3 mmol) was stirred overnight. LC/MS showed no starting material. The reaction was quenched via addition of a saturated solution of sodium bicarbonate and was extracted with DCM. The organic layer was washed with water (3×), dried over sodium sulfate and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in hexanes to afford the title compound (178 mg, 25%). LC/MS: Rt=1.24 min, ES+ 264 (AA standard).

Workup

  1. customThe reaction was quenched via addition of a saturated solution of sodium bicarbonate
  2. extractionwas extracted with DCM
  3. washThe organic layer was washed with water (3×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel chromatography
  7. washeluting with a gradient of 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-1e3564890bd74d739cb604b9b67590ff
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Linked notes

Loading…