Acetonitrile → 1,5-Diazabicyclo(4.3.0)non-5-ene

HRID 879019Notes

Reaction equation

HRID 879019 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C@@H:6]1[CH2:12][CH2:11][C@H:10]2[C@H](O2)C1)=O.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)S)C=CC=CC=1.[C:35](#[N:37])C>>[CH2:12]1[CH2:6][N:5]2[C:10](=[N:37][CH2:35][CH2:2][CH2:3]2)[CH2:11]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 866791002,2,2-trifluoro-N-[rel-(1R,3R,6S)-7-oxabicyclo[4.1.0]heptan-3-yl]acetamide

Product 1

HCID 763491,5-Diazabicyclo(4.3.0)non-5-ene

Procedure

1.55 g of 2,2,2-Trifluoro-N-(1R,3R,6S)-7-oxa-bicyclo[4.1.0]hept-3-yl-acetamide (Example 3 Step B), 2.46 g of triphenylmethanethiol and 25 mL of acetonitrile were charged to a flask. To the mixture obtained 880 μL of DBN was added, and the mixture obtained was heated to 60° C. and stirred for 23 h. Upon completion of the reaction (TLC), the mixture obtained was cooled to rt, diluted with EtOAc and washed with H2O and brine. The organic layer obtained was dried over MgSO4, concentrated in vacuo and the crude product obtained was subjected to column chromatography (eluent: Cyclohexane/EtOAc 5:1). The required fractions were identified, combined and concentrated in vacuo.

Sources & evidence

ORD record
ord-447bed7dae714231841d26a51ee9d2b0
Source dataset
uspto-grants-2015_03
Patent number
US08987498B2

Reaction notes

Loading…