Triethyl phosphite → HCID 86584892, compound

HRID 1170833Notes

Reaction equation

[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21]Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([O:26][P:27]([O:31]CC)[O:28][CH2:29][CH3:30])[CH3:25]>>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][P:27]([O:28][CH2:29][CH3:30])([O:26][CH2:24][CH3:25])=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 58096221HCID 58096221, compound

Product 1

HCID 86584892HCID 86584892, compoundYield 84%

Conditions

Temperature: 70 °C

Procedure

A mixture of (S)-1-(2-bromomethyl-benzoyl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (898 mg, 2.4 mmol) and triethylphosphite (432 mg, 2.4 mmol) was heated at 70° C. for 4 h. After cooling, the residue was purified by flash chromatography (ethyl acetate) to afford the title compound as a clear viscous oil (872 mg, 84%): 1H NMR (400 MHz, CDCl3) δ 1.17 (3H, t, J=7.0 Hz), 1.26 (3H, t, J=7.0 Hz), 1.53 (9H, s), 2.07-2.14 (1H, m), 2.43-2.69 (3H, m), 3.12 (1H, dd, J 22.4, 15.0 Hz), 3.62 (1H, dd, J 22.1, 15.0 Hz), 3.84-4.06 (4H, m), 4.87 (1H, dd, J 8.9, 4.8 Hz), 7.31-7.46 (4H, m).

Workup

temperatureAfter cooling
customthe residue was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-0ce52f8f174041959ad8e88451d71713
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829561B2

Reaction notes

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