Triethylamine → ethyl (1S,5S,6R)-7-acetyl-5-((tert-butoxycarbonyl)amino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate

HRID 1020389Notes

Reaction equation

HRID 1020389 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:15]([O:17][C:18]([C:20]1[CH2:25][C@H:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:23]([NH:34][C:35](=[O:37])[CH3:36])[C@H:22](O)[CH:21]=1)=[O:19])[CH3:16].CCN(CC)CC.CCCCCC.C(OCC)(=O)C>ClCCl>[C:35]([N:34]1[C@@H:22]2[C@H:23]1[C@@H:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][C:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])=[CH:21]2)(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5363146Diisopropyl azodicarboxylateHCID 21226206Ethyl acetate hexaneHCID 68364405(3R,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Product 1

HCID 11594989ethyl (1S,5S,6R)-7-acetyl-5-((tert-butoxycarbonyl)amino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (4° C.) solution of PhMe2P (71 mg; 0.52 mmol) in dichloromethane (1 mL) was added dropwise during 1 min DIAD (104 mg; 0.52 mmol). After additional 5 min of stirring a solution of alcohol 12 (84 mg; 0.24 mmol) and Et3N (7 μL; 0.05 mmol) in dichloromethane (1 mL) was added dropwise. After 10 min the reaction mixture was directly loaded on a silica column. Chromatography [hexane-ethyl acetate (3:1)→(2:1), 6 ml silica] afforded 53 mg (70%) of aziridine 13 as a colourless oil with trace amounts of 14.

Workup

  1. additionwas added dropwise

Sources & evidence

ORD record
ord-533639f3f8eb4d95bb3b4d026dd6b1dd
Source dataset
uspto-grants-2014_05
Patent number
US08716333B2

Reaction notes

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