3-(aminomethyl)-N,N-dimethylaniline → HCID 59570849, compound

HRID 2071179Notes

Reaction equation

HRID 2071179 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[N:6]([CH3:8])[CH3:7].[O:12]1[CH2:14][C@@H:13]1[C@@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[CH3:7][N:6]([CH3:8])[C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH2:2][NH:1][CH2:14][C@@H:13]([OH:12])[C@@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 27609383-(aminomethyl)-N,N-dimethylanilineHCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

Product 1

HCID 59570849HCID 59570849, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

3-(aminomethyl)-N,N-dimethylaniline (1.2 eq) was dissolved in the minimum amount of anhydrous CH2Cl2 under Ar, followed by the addition of tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (1 eq) with stirring. Anhydrous CH2Cl2 was added dropwise until all of the epoxide had dissolved. The reaction was heated to 50° C. After heating overnight all of the solvent was gone leaving a solid in the flask. Purification via flash chromatography yielded tert-butyl (2S,3R)-4-(3-(dimethylamino)benzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate.

Workup

  1. dissolutionhad dissolved
  2. temperatureAfter heating overnight all of the solvent
  3. customwas gone leaving a solid in the flask
  4. customPurification via flash chromatography

Sources & evidence

ORD record
ord-147ae0dc235645b4b025e4a6bf33e454
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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