Methyl iodide → HCID 68096871, compound

HRID 578618Notes

Reaction equation

HRID 578618 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.[H-].[Na+].I[CH3:25]>C1COCC1>[CH3:25][O:1][CH2:2][CH2:3][CH:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19104047HCID 19104047, compound

Product 1

HCID 68096871HCID 68096871, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [3-hydroxy-1-(3-nitrophenyl)propyl]carbamate (2 g; 6.75 mmol; 1.00 eq.) in anhydrous THF (10 mL) was added NaH (567 mg; 14.17 mmol; 2.10 eq.) at 0° C. The mixture was stirred for 20 minutes and iodomethane (1.53 g; 7.42 mmol; 1.10 eq.) was added. The mixture was stirred for 2 hours at 0° C. After work up, the crude product was purified by flash chromatography on silica gel (EtOAc:Hex=1:4) to provide 1.5 g of tert-butyl [3-methoxy-1-(3-nitrophenyl)propyl]carbamate.

Workup

  1. stirringThe mixture was stirred for 2 hours at 0° C
  2. customAfter work up, the crude product was purified by flash chromatography on silica gel (EtOAc:Hex=1:4)

Sources & evidence

ORD record
ord-c74a11f9a96b419bbc42d501b681b03d
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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