Magnesium → tert-butyl 2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate

HRID 2389552Notes

Reaction equation

HRID 2389552 reaction equation
S([N:11]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C:13]2[CH:26]=[CH:27][CH:28]=[CH:29][C:12]1=2)(C1C=CC(C)=CC=1)(=O)=O.[Mg]>CO>[NH:11]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH2:14][C:13]2[CH:26]=[CH:27][CH:28]=[CH:29][C:12]1=2

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 59400164tert-butyl 1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate

Product 1

HCID 59400102tert-butyl 2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamateYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (0.6 g, 1.4 mmol) in methanol (33 mL) was added magnesium metal turnings (0.51 g, 0.021 mol). The reaction mixture was stirred for 4 hours at room temperature before being evaporated to dryness and diluted with dichloromethane. The suspension formed was filtered through celite and the filtrate washed with brine. The organic layer was dried over anhydrous sodium sulfate concentrated under vacuo to give a residue which was purified by silica gel column chromatography eluting with (0-10% ethyl acetate in hexanes) to afford tert-butyl 2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (0.3 g). 1H NMR: (400 MHz, CDCl3) δ: 7.18-7.08 (m, 2H), 6.92 (t, 1H), 6.84 (d, 1H), 4.52 (bs, 1H), 3.92 (m, 1H), 3.78 (bs, 1H), 3.14-2.98 (m, 2H), 3.88-3.78 (m, 1H), 2.06-2.0 (m, 1H), 1.96-1.88 (m, 1H), 1.6 (bs, 1H), 1.42 (s, 9H).

Workup

  1. custombefore being evaporated to dryness
  2. additiondiluted with dichloromethane
  3. customThe suspension formed
  4. filtrationwas filtered through celite
  5. washthe filtrate washed with brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuo
  8. customto give a residue which
  9. customwas purified by silica gel column chromatography
  10. washeluting with (0-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ff371537f2d44ac3bb4448231aeb2c99
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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