Trichloro[(methylsulfanyl)methane]boron → 2-Pyrrolidone

HRID 880033Notes

Reaction equation

HRID 880033 reaction equation
ClC1C=C([C@@H]2C3C(=CC=CC=3)[C@H](NC([C:22]3[CH:27]=[CH:26][N:25](C)[C:24](=[O:29])[C:23]=3[OH:30])=O)CC2)C=CC=1Cl.[B-](Cl)(Cl)(Cl)[S+](C)C>C(Cl)Cl.ClCCCl>[NH:25]1[CH2:26][CH2:27][CH2:22][C:24]1=[O:29].[NH:25]1[CH2:26][CH2:27][CH2:22][C:23](=[O:30])[C:24]1=[O:29]

Participants

6

Reactant 2

HCID 16211690Trichloro[(methylsulfanyl)methane]boronHCID 86730085HCID 86730085, compound

Product 2

HCID 120252-PyrrolidoneHCID 5163733Piperidine-2,3-dione

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of Example 8A (13 mg, 0.028 mmol) in DCM (0.5 mL) and DCE (0.5 mL) was added boron trichloride-methyl sulfide complex (30.6 mg, 0.171 mmol). The reaction mixture was stirred at 70° C. for 16 h. The reaction mixture was quenched with ice and MeOH and example 8 isolated via prep HPLC (10 minute gradient from 5 to 100% B; Column: Phenomenex AXIA Luna 100×20 mm 5 μm; Solvent A: 10% ACN-90% H2O-0.1% TFA; Solvent B: 90% ACN-10% H2O-0.1% TFA). The desired fractions were evaporated to dryness to give Example 8 (5 mg, 0.01 mmol, 40% yield). LCMS RT=2.27 min, [M+1]=443.1 {(MeOH/H2O/TFA) Phenom. Luna C18; 50×4.6 mm; 4 min Grad}; HPLC (150×4.6 mm 3.5 μm, 254 nm): Sunfire {RT=11.2 min, 95%}; Xbridge {RT=9.9 min, 96.3%}. 1H NMR (500 MHz, MeOD) δ ppm 2.01-2.06 (m, 3H) 2.19-2.25 (m, 1H) 3.59 (s, 3H) 4.20 (t, J=6.33 Hz, 1H) 5.33 (t, J=5.64 Hz, 1H) 6.74 (d, J=7.43 Hz, 1H) 6.86 (d, J=7.70 Hz, 1H) 7.10 (dd, J=8.25, 1.93 Hz, 1H) 7.14 (d, J=7.43 Hz, 1H) 7.18 (t, J=7.57 Hz, 1H) 7.24 (t, J=7.29 Hz, 1H) 7.34 (d, J=2.20 Hz, 1H) 7.39 (d, J=7.43 Hz, 1H) 7.43-7.46 (m, 1H).

Workup

  1. customThe reaction mixture was quenched with ice and MeOH and example 8

Sources & evidence

ORD record
ord-fa90da82113247e5b7156f220f13fce1
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

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