Potassium Carbonate → 6-(4-Bromobenzyl)-2-oxa-6-aza-spiro[3.3]heptane

HRID 1888442Notes

Reaction equation

HRID 1888442 reaction equation
[CH2:1]1[C:4]2([CH2:7][NH:6][CH2:5]2)[CH2:3][O:2]1.[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.[I-].[Na+]>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:6]2[CH2:7][C:4]3([CH2:3][O:2][CH2:1]3)[CH2:5]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 231118872-Oxa-6-azaspiro[3.3]heptane

Product 1

HCID 582664706-(4-Bromobenzyl)-2-oxa-6-aza-spiro[3.3]heptaneYield 68%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-oxa-6-aza-spiro[3.3]heptane (˜3.72 mmol), 4-bromobenzyl bromide (0.39 g, 1.54 mmol), potassium carbonate (0.64, 4.63 mmol) and sodium iodide (11 mg, 0.08 mmol) in THF (10 mL) was stirred at ambient temperature for 16 h. The solid was removed by filtration, washed with THF and the combined filtrate was evaporated. The resultant residue was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in pentane then 10% methanol in DCM) to afford the title compound (0.28 g, 68%) as a viscous oil which crystallised on standing to a pale yellow solid. 1H NMR (CDCl3, 300 MHz): 7.46-7.40 (m, 2H), 7.15-7.09 (m, 2H), 4.73 (s, 4H), 3.48 (s, 2H), 3.35 (s, 4H).

Workup

  1. customThe solid was removed by filtration
  2. washwashed with THF
  3. customthe combined filtrate was evaporated
  4. customThe resultant residue was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in pentane

Sources & evidence

ORD record
ord-686bc9cb7f0c4c728ee1b0288bb7220a
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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