Methyl iodide → HCID 19610437, compound

HRID 1602096Notes

Reaction equation

HRID 1602096 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:26]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][O:17][CH3:26])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19610443tert-Butyl 4-(3-hydroxy-2-phenylpropyl)piperazine-1-carboxylate

Product 1

HCID 19610437HCID 19610437, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 2 (0.60 g, 1.88 mmol) in anhydrous DMF (20 ml), at 0° C., was added sodium hydride (0.113 g of a 60% dispersion in oil, 2.81 mmol) and the mixture stirred for 0.2 h, before adding methyl iodide (0.399 g, 2.81 mmol), dropwise. The mixture was warmed to room temperature, stirred for 2 h, and then partitioned between water and ethyl acetate. The organic phase was separated and washed with water (×2) and brine (×1). After drying (MgSO4), the solvent was removed in vacuo and the crude product chromatographed through silica gel eluting with ethyl acetate/hexane (1:1) to give the desired methyl ether (0.365 g, 60%), δ(250 MHz, CDCl3) 1.44 (9H, s, (Me)3), 2.26-2.78 (6H, m, 3 of CH2), 3.02-3.16 (1H, m, CH), 3.31 (3H, s, OMe). 3.34-3.40 (4H, m, 2 of CH2), 3.53-3.69 (2H, m, CH2), 7.19-7.34 (5H, m, Ar-H).

Workup

  1. stirringstirred for 2 h
  2. custompartitioned between water and ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with water (×2) and brine (×1)
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customthe crude product chromatographed through silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-b5d479c5072747cebc847b6dc388bea8
Source dataset
uspto-grants-1999_11
Patent number
US05981529

Reaction notes

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