Triethylamine → 3-(tert-Butyloxycarbonyl)-7-methanesulfonyloxy-2,3,4,5tetrahydro-1H-3-benzazepine

HRID 395272Notes

Reaction equation

HRID 395272 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18173274tert-butyl 7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

Product 1

HCID 112792893-(tert-Butyloxycarbonyl)-7-methanesulfonyloxy-2,3,4,5tetrahydro-1H-3-benzazepineYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(tert-butyloxycarbonyl)-7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine (3.0 g, 0.011 mol), methanesulphonylchloride (1.44 g, 0.013 mol), triethylamine (1.27 g, 0.013 mol) and dichloromethane (50 ml) was stirred at room temperature for 18 h. The reaction mixture was then partitioned between dichloromethane (50 ml) and a saturated solution of sodium hydrogen carbonate (50 ml). The organic layer was separated, washed with water (50 ml) and then dried (Na2SO4). The solvent was then evaporated in vacuo to give the title compound (3.85 g, 99%) as a pale yellow oil.

Workup

  1. customThe reaction mixture was then partitioned between dichloromethane (50 ml)
  2. customThe organic layer was separated
  3. washwashed with water (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was then evaporated in vacuo

Sources & evidence

ORD record
ord-0c5b50615dda4b10bf689f8a32d65a8d
Source dataset
uspto-grants-2003_08
Patent number
US06605607B1

Reaction notes

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