Triethyl phosphite → HCID 131716301, compound

HRID 1164864Notes

Reaction equation

HRID 1164864 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][CH2:14]Br)[CH2:10][C@@H:9]1[C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[P:20]([O:27]CC)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][CH2:14][P:20]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:27])[CH2:10][C@@H:9]1[C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 96536729HCID 96536729, compound

Product 1

HCID 131716301HCID 131716301, compound

Procedure

A mixture of 0.60 g of cis methyl N-t-butoxycarbonyl-4-(2-bromoethyl)pyrrolidine-2-carboxylate and 3 ml triethyl phosphite is refluxed for 2 hours. The excess triethyl phosphite is distilled off under vacuum and the residue is flash chromatographed with methylene chloride/methanol (95:5) to afford cis methyl N-t-butoxycarbonyl-4-(2-diethylphosphonoethyl)pyrrolidine-2-carboxylate.

Workup

  1. temperatureis refluxed for 2 hours
  2. distillationThe excess triethyl phosphite is distilled off under vacuum
  3. customchromatographed with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-07c1dea41eb34f5d957059dad8cff01d
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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