Ammonium Hydroxide → N-Despropyl-rotigotine

HRID 2106631Notes

Reaction equation

HRID 2106631 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:20]C)[CH2:11]1.B(Br)(Br)Br.[NH4+].[OH-]>ClCCl>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[OH:20])[CH2:11]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 135643635-Methoxy-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride

Product 1

HCID 15107528N-Despropyl-rotigotineYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.95 g (0.015 mol) of the product of Step 3 in dry dichloromethane was added 80 mL of boron tribromide under N2. The mixture was stirred 1 hour at room temperature then poured over NH4OH and ice. The organic layer was separated and dried over MgSO4, and concentrated to yield 1.0 g of product: NMR (CDCl3)δ7.2-6.6(6H,m), 3.1-2.8(7H,m), 2.7-2.5(2H,m), 2.15(1H,m), 1.65(1H,m).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-966f6e4454fb474695a54b6a34ce5442
Source dataset
uspto-grants-1990_06
Patent number
US04931270

Reaction notes

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