Hydrogen Bromide → [7-(2-Amino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester

HRID 2177127Notes

Reaction equation

HRID 2177127 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[NH:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([CH2:16][CH2:17][NH:18]C(OCC3C=CC=CC=3)=O)=[CH:11][CH:12]=2)[CH:7]1[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)[CH3:2].Br>C(O)(=O)C.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:37])[NH:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([CH2:16][CH2:17][NH2:18])=[CH:11][CH:12]=2)[CH:7]1[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)[CH3:2]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 57476722[7-(2-Benzyloxycarbonylamino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester

Product 1

HCID 57467359[7-(2-Amino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl esterYield 105.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To [7-(2-benzyloxycarbonylamino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-carbamic acid ethyl ester (500 mg, 0.960 mmol) was added at room temperature 8 ml of 33% HBr in acetic acid. After 2 h the mixture was diluted with CH2Cl2, washed twice with NaHCO3, dried and filtered. The solvent was evaporated to obtain the product as a yellow oil (392 mg), which was used without further purification.

Workup

  1. washwashed twice with NaHCO3
  2. customdried
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1640a50635b74db8b28fb97b497f7884
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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