Trimethylsilyl iodide → HCID 10287285, compound

HRID 1454340Notes

Reaction equation

HRID 1454340 reaction equation
[CH2:1]([C:10]1[CH:30]=[CH:29][C:13]([CH2:14][N:15]2[CH2:19][CH2:18][C:17]([P:21](=[O:28])([O:25]CC)[O:22]CC)([OH:20])[CH2:16]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].I[Si](C)(C)C>C(Cl)(Cl)Cl>[CH2:1]([C:10]1[CH:30]=[CH:29][C:13]([CH2:14][N:15]2[CH2:19][CH2:18][C:17]([P:21](=[O:22])([OH:25])[OH:28])([OH:20])[CH2:16]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131727246HCID 131727246, compound

Product 1

HCID 10287285HCID 10287285, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 33 mg (0.075 mmol) of (R/S)-1-(4-nonylbenzyl)-3-hydroxypyrrolidin-3-ylphosphonic acid, diethyl ester (from Step E) in 1 mL of chloroform was treated with 0.053 mL (0.37 mmol) of iodotrimethylsilane. The reaction was allowed to stir at rt for 1 h. The reaction was quenched with MeOH and concentrated several times from MeOH. The residue was purified using LC-2 to afford 4.6 mg (16%) of the title compound: ESI-MS 385 (M+H); LC-1: 3.01 min.

Workup

  1. customThe reaction was quenched with MeOH
  2. concentrationconcentrated several times from MeOH
  3. customThe residue was purified

Sources & evidence

ORD record
ord-c08569ae59e74bff96317bd9b354a40a
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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