(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → tert-butyl (2S,3R)-4-(3-(diethylamino)benzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

HRID 2071176Notes

Reaction equation

[Al](OS(C(F)(F)F)(=O)=O)(OS(C(F)(F)F)(=O)=O)OS(C(F)(F)F)(=O)=O.[NH2:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=1)[N:31]([CH2:34][CH3:35])[CH2:32][CH3:33].[O:39]1[CH2:41][C@@H:40]1[C@@H:42]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CCOC(C)=O.O>[CH2:34]([N:31]([CH2:32][CH3:33])[C:30]1[CH:29]=[C:28]([CH:38]=[CH:37][CH:36]=1)[CH2:27][NH:26][CH2:41][C@@H:40]([OH:39])[C@@H:42]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:55])([CH3:54])[CH3:56])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH3:35]

Participants

Conditions

Temperature: 70 °C

Procedure

Al(OTf)3 (0.0168 g, 0.036 mmol, 5 mol %) was added to a flask charged with 3-(aminomethyl)-N,N-diethylaniline (0.19 g, 1.07 mmol, 1.5 eq) under Ar. After stirring for 10 min tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (0.187 g, 0.71 mmol, 1 eq) was added and the mixture was heated to 70° C. for 1 h. After cooling to room temperature the residue was dissolved in EtOAc with a few drops of water. After 20 min of vigorous stirring the mixture was filtered through cotton and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.0682 g (0.154 mmol, 22% yield) of the product.

Workup

additionwas added
temperatureAfter cooling to room temperature the residue
filtrationwas filtered through cotton
dry with materialdried over Na2SO4
filtrationThe inorganics were filtered off
customthe solvent was removed in vacuo
customPurification via flash chromatography

Sources & evidence

ORD record: ord-06b7f7cab80a4d7989d8d051ed5376fc
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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