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

HRID 879018Notes

Reaction equation

HRID 879018 reaction equation
[C@H]12O[C@H:6]1[CH2:5][CH2:4][C@@H:3]([NH:8][C:9](=O)OC(C)(C)C)C2.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)S)C=CC=CC=1.[C:36](#[N:38])[CH3:37]>>[CH2:4]1[CH2:3][N:8]2[C:6](=[N:38][CH2:36][CH2:37][CH2:9]2)[CH2:5]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 86679102HCID 86679102, compound

Product 1

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

Procedure

1 g of tert-butyl (1R,3R,6S)-(7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamate (Example 1 Step E), 1.56 g of triphenylmethanethiol, and 16.4 mL of acetonitrile were charged to a flask. To the mixture obtained 560 μL of DBN was added, and the mixture obtained was heated to 40° C. and stirred for 22.5 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-317581bf45784f2284cb37f7fdb6812d
Source dataset
uspto-grants-2015_03
Patent number
US08987498B2

Reaction notes

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