Trifluoroacetic acid → 7-Methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 395273Notes

Reaction equation

HRID 395273 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:23][S:20]([O:19][C:17]1[CH:16]=[CH:15][C:12]2[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=2[CH:18]=1)(=[O:21])=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 112792893-(tert-Butyloxycarbonyl)-7-methanesulfonyloxy-2,3,4,5tetrahydro-1H-3-benzazepine

Product 1

HCID 112994727-Methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepineYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(tert-butyloxycarbonyl)-7-methanesulphonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine (3.8 g, 0.011 mol), trifluoroacetic acid (3.76 g, 0.033 mol) and dichloromethane (50 ml) was heated at 50° C. for 5 h. The solvents were then evaporated in vacuo and the residue partitioned between water (200 ml) and ethyl acetate (150 ml). The aqueous layer was removed and washed with ethyl acetate (100 ml) and then basified to pH 14 with 40% sodium hydroxide. The suspension was then extracted with ethyl acetate (3×150 ml) and the combined organic layers dried (Na2SO4). The solvents were evaporated in vacuo to give the title compound (2.15 g, 80%) as a colourless oil.

Workup

  1. customThe solvents were then evaporated in vacuo
  2. customthe residue partitioned between water (200 ml) and ethyl acetate (150 ml)
  3. customThe aqueous layer was removed
  4. washwashed with ethyl acetate (100 ml)
  5. extractionThe suspension was then extracted with ethyl acetate (3×150 ml)
  6. dry with materialthe combined organic layers dried (Na2SO4)
  7. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-6d919e89670b45d884d40bc653debc9f
Source dataset
uspto-grants-2003_08
Patent number
US06605607B1

Reaction notes

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