Sodium hydride → 1-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidine

HRID 1181352Notes

Reaction equation

HRID 1181352 reaction equation
[CH3:1][C:2]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)([CH3:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[O:23][CH3:24]>CN(C=O)C.CCOC(C)=O>[CH3:24][O:23][C:15]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=1[O:4][CH2:3][C:2]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)([CH3:5])[CH3:1]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 705192-Chloro-5-nitroanisoleHCID 223118122-Methyl-2-(pyrrolidin-1-yl)propan-1-ol

Product 1

HCID 589807741-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidineYield 12.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-2-pyrrolidin-1-ylpropan-1-ol (0.3776 g, 2.0682 mmol) was taken up in anhydrous DMF (5 mL). Sodium hydride (0.083 g of a 60% dispersion, 2.0682 mmol) was added. The reaction was stirred at RT until gas evolution was complete. 1-Chloro-2-methoxy-4-nitrobenzene (0.3578 g, 2.0682 mmol) was added. The reaction was heated to 80° C. and stirred for 72 h. Cooled to RT and diluted with EtOAc, (50 mL) and washed with water (3×50 mL). Organics were dried over MgSO4, filtered and concentrated. Crude product was purified by chromatatron (100% CH2Cl2 to 95:5 CH2Cl2:MeOH) to give 0.075 g (0.2551 mmol, 12%) of the product. 1H NMR (CDCl3) δ 7.81 (d, 1H, J=8.8 Hz), 7.73 (s, 1H), 7.15 (d, 1H, J=8.8 Hz), 3.88 (s, 3H), 2.76 (s, 2H), 2.68 (bs, 4H), 1.75 (bs, 4H), 1.38 (s, 6H).

Workup

  1. temperatureThe reaction was heated to 80° C.
  2. stirringstirred for 72 h
  3. temperatureCooled to RT
  4. washwashed with water (3×50 mL)
  5. dry with materialOrganics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrude product was purified by chromatatron (100% CH2Cl2 to 95:5 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-c1a31f03d4a6419195b3cb638c0b0077
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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