Methyl iodide → HCID 53415283, compound

HRID 1506943Notes

Reaction equation

HRID 1506943 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:22])[CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 16244608tert-Butyl 3-(benzylamino)azetidine-1-carboxylate

Product 1

HCID 53415283HCID 53415283, compoundYield 425.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl 3-(benzylamino)azetidine-1-carboxylate (13a) (0.55 gm, 2.09 mmol) in DMF was added methyl iodide (0.26 ml, 4.18 mmol) and cesium carbonate (1.36 gm, 4.18 mmol). The resultant reaction mixture was then warmed to 60° C. and stirred for 2 h. The reaction mixture was then diluted with ethyl acetate (100 ml), washed with water (3×25 ml), brine, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography to give compound (13b) (2.46 gm, 72%). 1H NMR (400 MHz, CDCl3) δ: 1.40 (s, 9H), 3.40 (m, 5H), 4.00 (m, 2H), 4.20 (m, 2H), 5.2 (m, 1H), 7.50 (m, 3H), 7.70 (d, 2H); MS: m/z 277.10 (M+1)+.

Workup

  1. customThe resultant reaction mixture
  2. washwashed with water (3×25 ml), brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-795f88b52e2b4ffab74cff642bce2ad6
Source dataset
uspto-grants-2015_12
Patent number
US09221792B2

Reaction notes

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