Dimethylamine → HCID 58580003, compound

HRID 1670893Notes

Reaction equation

HRID 1670893 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH:5]1[CH:11]([OH:12])[CH2:10][CH:9]2[CH:6]1[CH2:7][CH2:8]2.C1C[O:16]CC1>CC(C)=O>[CH3:1][N:2]([CH3:3])[CH:9]1[CH:10]2[CH:11]([OH:12])[CH2:5][CH:6]1[C:7](=[O:16])[CH2:8]2

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 13087128HCID 13087128, compound

Product 1

HCID 58580003HCID 58580003, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of dimethylamine (2.0 M, 24 ml, 48 mmol) in THF was added to a solution of 2-bromo-bicyclo[3.2.0]heptan-3-ol (4.00 g, 19.5 mmol) in acetone (40 ml) at 0° C. and the mixture allowed to warm to ambient temperature over 1 h and stirred at ambient temperature overnight. The orange solution was filtered and the filtrate was evaporated to dryness. Purification was achieved by column chromatography on silica gel using 5% MeOH in DCM to yield 3.01 g (91%) of the product as a tan powder. LC-MS (Method 2): Rt 0.37 min, m/z 170.09 [MH]+.

Workup

  1. filtrationThe orange solution was filtered
  2. customthe filtrate was evaporated to dryness
  3. customPurification

Sources & evidence

ORD record
ord-986052cdd84b408e9c786a35e89442af
Source dataset
uspto-grants-2011_08
Patent number
US07994211B2

Reaction notes

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