Chlorosuccinimide → Tert-butyl [8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate

HRID 577518Notes

Reaction equation

HRID 577518 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:8]=[C:9]([O:12][CH:13]([CH3:15])[CH3:14])[CH:10]=2)[CH2:5][CH2:4][NH:3]1.C1C(=O)N([Cl:31])C(=O)C1>CC#N>[Cl:31][C:10]1[C:9]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[C:6]2[C:11]=1[C:2](=[O:1])[NH:3][CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86723744Tert-butyl [1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate

Product 1

HCID 86723745Tert-butyl [8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamateYield 92.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl [1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate (77b, 875 mg, 2.73 mmol) and NCS (401 mg, 3.00 mmol) in MeCN (80 mL) was stirred at 75° C. for 2 hours. After cooling down to room temperature and concentrating under vacuum, the resulting residue was purified by column chromatography (0-100% EtOAc/heptanes) to give tert-butyl [8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinolin-5-yl]carbamate (77c, 893 mg, 92%) as a solid.

Workup

  1. concentrationconcentrating under vacuum
  2. customthe resulting residue was purified by column chromatography (0-100% EtOAc/heptanes)

Sources & evidence

ORD record
ord-b23b9c460fb342559d901373c3aee941
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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