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

HRID 33212
Notes
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Reaction equation

HRID 33212 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344Dichloromethane
Solvent

Procedure

A solution of 3-(tert-butyloxycarbonyl)-7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine (3.0 g, 0.011 mol), methanesulfonylchloride (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-cb9607fd695f4594a7900c83431f560f
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429579B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes