Ethyl 4-bromobutyrate → Ethyl 4-[5-phenylsulphonamido-1,2,3,4-tetrahydroisoquinolin-2-yl]butyrate

HRID 1194104Notes

Reaction equation

HRID 1194104 reaction equation
Cl.[C:2]1([S:8]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][NH:16][CH2:17]3)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[C:2]1([S:8]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][N:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:17]3)(=[O:10])=[O:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 212717485-Phenylsulphonamido-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 21271751Ethyl 4-[5-phenylsulphonamido-1,2,3,4-tetrahydroisoquinolin-2-yl]butyrate

Procedure

5-Phenylsulphonamido-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.7 g) was reacted with ethyl 4-bromobutyrate in the manner described in Example 2(a). After elution from a silica column with ethyl acetate:methanol mixtures, the product was recrystallised from ethanol to give ethyl 4-[5-phenylsulphonamido-1,2,3,4-tetrahydroisoquinolin-2-yl]butyrate as a white solid (2.0 g).

Workup

  1. washAfter elution from a silica column with ethyl acetate
  2. custommethanol mixtures, the product was recrystallised from ethanol

Sources & evidence

ORD record
ord-bf646b4f8fc34e2da77ab3aba5ae5b8f
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

Loading…