Triethylamine → HCID 67214908, compound

HRID 2421363Notes

Reaction equation

HRID 2421363 reaction equation
Cl.[C@H:2]12[CH2:8][C@H:5]([O:6][CH2:7]1)[CH2:4][NH:3]2.[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:3]2[CH2:4][C@@H:5]3[CH2:8][C@H:2]2[CH2:7][O:6]3)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride

Product 1

HCID 67214908HCID 67214908, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1S,4S)-(+)-2-Aza-5-oxabicyclo[2.2.1]heptane hydrochloride (1.26 g), 4-bromobenzyl bromide (2.32 g) and triethylamine (3.88 ml) were stirred in dimethylformamide (30 ml) for 18 h. The mixture was partitioned between diethyl ether (60 ml) and water (60 ml) and the organic phase was washed further with water (60 ml), dried (MgSO4), concentrated in vacuo and purified by Bondelute® chromatography, eluting with 0-100% ethyl acetate/iso-hexane to give the product as an orange oil (1.91 g).

Workup

  1. customThe mixture was partitioned between diethyl ether (60 ml) and water (60 ml)
  2. washthe organic phase was washed further with water (60 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by Bondelute® chromatography
  6. washeluting with 0-100% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-fa24347d46bc4cfc871f6a3519b18b60
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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