Methyl iodide → HCID 89499091, compound

HRID 588700Notes

Reaction equation

HRID 588700 reaction equation
[N:1]1([CH2:6][C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:5]=[CH:4][CH:3]=[N:2]1.[Li][CH2:28]CCC.IC>O1CCCC1>[CH3:28][C:5]1[N:1]([CH2:6][C:7]23[CH2:14][CH:13]4[CH2:12][CH:11]([CH2:10][C:9]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])([CH2:15]4)[CH2:8]2)[CH2:16]3)[N:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 89498881HCID 89498881, compoundHCID 178418339Butyllithium

Product 1

HCID 89499091HCID 89499091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.) solution of EXAMPLE 83A (1.0 g) in tetrahydrofuran (10 mL) was added n-BuLi (5 mL, 2.5 M in hexane). The reaction mixture was stirred for 90 minutes, and iodomethane (1 mL) was added. The reaction mixture was stirred at −78° C. for 90 minutes and quenched by the addition of 1 drop of trifluoroacetic acid. The reaction mixture was warmed to room temperature and concentrated to dryness. The residue was used in the subsequent step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 90 minutes
  2. customquenched by the addition of 1 drop of trifluoroacetic acid
  3. concentrationconcentrated to dryness
  4. customThe residue was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-076b4adc4ff54b9e942e7cd93a8d3ac8
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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