Chloromethyl Methyl Ether → HCID 69269890, compound

HRID 751533Notes

Reaction equation

HRID 751533 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:23][OH:24])[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27][O:28][CH2:29]Cl.C(OCC)(=O)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:23][O:24][CH2:27][O:28][CH3:29])[CH:16]=[CH:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69269462HCID 69269462, compound

Product 1

HCID 69269890HCID 69269890, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-(7-hydroxymethylindol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (0.25 g, 0.76 mmol) in 5 mL of tetrahydrofuran and add sodium hydride (36 mg, 1.5 mmol) at room temperature. After 40 minutes, add methoxymethyl chloride (0.11 mL, 1.5 mmol) and stir the mixture for 4 hours. Concentrate the reaction and subject it to flash chromatography using 5:1 hexanes:ethyl acetate to give 0.23 g product. FAB MS 374.

Workup

  1. concentrationConcentrate
  2. customthe reaction

Sources & evidence

ORD record
ord-68c2e5a5845543b79c518aa6b08c45b2
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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