Triethylamine → N-methyl-N-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethyl]-2-aminoethanol

HRID 487220Notes

Reaction equation

HRID 487220 reaction equation
CNC([OH:5])C.[CH3:6][C:7]1([CH3:17])[C@H:12]2[CH2:13][C@@H:8]1[CH2:9][CH2:10][C@H:11]2[CH2:14][CH2:15]Br.[CH2:18]([N:20]([CH2:23]C)CC)[CH3:19]>>[CH3:23][N:20]([CH2:15][CH2:14][C@@H:11]1[CH2:10][CH2:9][C@H:8]2[CH2:13][C@@H:12]1[C:7]2([CH3:17])[CH3:6])[CH2:18][CH2:19][OH:5]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 5247031N-MethylaminoethanolHCID 22850929(1S,2S,5S)-2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Product 1

HCID 22850950N-methyl-N-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethyl]-2-aminoethanol

Procedure

3.4 ml N-methylaminoethanol and 7.3 ml triethylamine were added to 12.4 g 2-((1S,2S,5S)-6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethyl bromide, and the reaction mixture was stirred for 6 hours at room temperature. To work up the reaction mixture it was chromatographed over silica gel using dichloromethane/methanol (8:2) as solvent. 3.8 g N-methyl-N-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethyl]-2-aminoethanol were obtained. Rf value=0.4. Furthermore, 7 g unreacted starting material were recovered.

Workup

  1. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-3b917bd3c4394f31aa22d87034678140
Source dataset
uspto-grants-1994_03
Patent number
US05294638

Reaction notes

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