Diisopropylethylamine → HCID 53357029, compound

HRID 2410335Notes

Reaction equation

HRID 2410335 reaction equation
[Cl-].[CH2:2]([O:6][C:7]1[C:12]2[C:13]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH2+:21][CH2:20][CH2:19]3)=[N:14][O:15][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH:3]([CH3:5])[CH3:4].[O:24]1[C:26]2([CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:25]1.C(N(CC)C(C)C)(C)C>C(O)C>[CH2:2]([O:6][C:7]1[C:12]2[C:13]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH2:25][C:26]4([OH:24])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH2:20][CH2:19]3)=[N:14][O:15][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1604391,6-Dioxaspiro[2.5]octaneHCID 69316976HCID 69316976, compound

Product 1

HCID 53357029HCID 53357029, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-{[(isobutoxy-1,2-benzisoxazol-3-yl)oxy]methyl}piperidinium chloride (40.9 mg, 0.120 mmol, EXAMPLE 8, step 4), 1,6-dioxaspiro[2.5]octane (30.4 mg, 0.266 mmol, Phosphorus and Sulfur and Related Elements 1984, 19, 113) and N,N-diisopropylethylamine (0.10 mL, 0.58 mmol) in ethanol (1 mL) was stirred overnight at room temperature. Solvent was evaporated, and the residual oil was purified by NH gel column chromatography (hexane/ethyl acetate 4:1) to give 34.0 mg (68%) of the title compound as a colorless oil.

Workup

  1. customSolvent was evaporated
  2. customthe residual oil was purified by NH gel column chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-b79900ec7e534822a63309e73c09ec30
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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