Trimethyl phosphite → [[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-methyl]phosphonic acid, dimethyl ester

HRID 2298080Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:23])=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9].[CH3:24][O:25][P:26]([O:29]C)[O:27][CH3:28]>>[Cl:23][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][P:26](=[O:29])([O:27][CH3:28])[O:25][CH3:24])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:13][CH:14]3[CH2:20][CH:18]([CH2:17][CH:16]([CH2:15]3)[CH2:21]1)[CH2:19]2)=[O:9]

Participants

Reactant 2

HCID 8472Trimethyl phosphite

HCID 219000205-Bromomethyl-2chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 86758648[[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-methyl]phosphonic acid, dimethyl ester

Procedure

5-Bromomethyl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (5.70 g, Example 8b) in 100 ml of trimethylphosphite was heated at reflux for 15 h. The solvent was removed by azeotropic distillation with toluene under high vacuum to afford the subtitle compound as a yellow solid.

Workup

temperatureat reflux for 15 h
customThe solvent was removed by azeotropic distillation with toluene under high vacuum

Sources & evidence

ORD record: ord-503b322c637145b6b3dd5c5d1e46562d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492355B1

Reaction notes

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