Sodium hydride → HCID 86653003, compound

HRID 1850875Notes

Reaction equation

HRID 1850875 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([OH:21])[CH:19]=4)[CH2:14][CH2:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:24]([NH:31][CH2:32][CH2:33]Br)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C)C=O>[C:27]([O:26][C:24](=[O:25])[NH:31][CH2:32][CH2:33][O:21][C:18]1[CH:19]=[C:20]2[C:15]([CH2:14][CH2:13][N:12]=[C:11]2[C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:10][CH2:9]2)=[CH:16][CH:17]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66868903HCID 66868903, compound

Product 1

HCID 86653003HCID 86653003, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[1-(4-chlorophenyl)cyclopropyl]-3,4-dihydroisoquinolin-7-ol (120 mg, 0.4 mmol) was added in several portions to a suspension of sodium hydrid (NaH, 1.3 mmol, activated by removal of oil) in dimethylformamide (DMF, 5 ml). 2-(Boc-amino)ethyl bromide was added after one hour and the resulting mixture stirred for 3 days at room temperature. DMF was evaporated, the residue diluted with ethylacetate and extracted with water. Removal of the solvents from the dried (Na2SO4) extract afforded an oil which was further purified by chromatography. Yield: 100 mg (0.23 mmol, 56%)

Workup

  1. customDMF was evaporated
  2. additionthe residue diluted with ethylacetate
  3. extractionextracted with water
  4. customRemoval of the solvents from the
  5. dry with materialdried (Na2SO4)
  6. extractionextract
  7. customafforded an oil which
  8. customwas further purified by chromatography

Sources & evidence

ORD record
ord-062312fc3d7f4059a07aea8f7c982d84
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

Loading…