Sodium hydride → HCID 86653003, compound

HRID 242095Notes

Reaction equation

HRID 242095 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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:33][CH2:32][NH:31][C:24](=[O:25])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=4)[CH2:14][CH2:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

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-c0471b9ea12c440a8e6f6d744e8f3d39
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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