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

HRID 2389551Notes

Reaction equation

HRID 2389551 reaction equation
[S:1]([N:11]1[CH2:17][CH2:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][C:13]2[CH:26]=[CH:27][CH:28]=[CH:29][C:12]1=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[H][H]>CO.[Pd]>[S:1]([N:11]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:14][C:13]2[CH:26]=[CH:27][CH:28]=[CH:29][C:12]1=2)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

5

Reactant 2

HCID 59400171tert-butyl 1-tosyl-2,3-dihydro-1H-benzo[b]azepin-4-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59400164tert-butyl 1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamateYield 840.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 1-tosyl-2,3-dihydro-1H-benzo[b]azepin-4-ylcarbamate (4.5 g, 0.001 mol) in methanol (120 mL), 10% palladium on carbon (0.5 g) was added. The reaction mixture was stirred under 1 atmosphere of hydrogen for 4 days. The reaction mixture was filtered and concentrated to dryness to give a residue which was purified by silica gel column chromatography eluting with (0-10% ethyl actetae in hexane) to afford tert-butyl 1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (3.5 g). 1H NMR: (400 MHz, CDCl3) δ: 7.54 (d, 1H), 7.40 (d, 2H), 7.18-7.08 (m, 4H), 7.06 (d, 1H), 6.38 (s, 1H), 5.65 (s, 1H), 3.86-3.82 (m, 2H), 2.78-2.74 (m, 2H), 2.18 (bs, 3H), 1.44 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to dryness
  3. customto give a residue which
  4. customwas purified by silica gel column chromatography
  5. washeluting with (0-10% ethyl actetae in hexane)

Sources & evidence

ORD record
ord-d8b12b15971946359780adc4bd5c442d
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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