Ruthenium → HCID 131724488, compound

HRID 1883310Notes

Reaction equation

HRID 1883310 reaction equation
[C:1]1([P:7]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:8]2[CH:52]=[CH:51][CH:50]=[CH:49][C:9]=2[CH2:10][NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[NH:18][CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]=[CH2:35])=[CH:30][CH:29]=3)[CH:23]=[CH:22][C:21]=2[P:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(C)=O.CS(C)=O.CS(C)=O.CS(C)=O.[Cl:75][Ru:76][Cl:77].[Ru]>C1(C)C=CC=CC=1>[C:53]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:52]=[CH:51][CH:50]=[CH:49][C:9]=2[CH2:10][NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[NH:18][CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]=[CH2:35])=[CH:30][CH:29]=3)[CH:23]=[CH:22][C:21]=2[P:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1.[Ru:76]([Cl:77])[Cl:75]

Participants

5

Reactant 3

HCID 23950RutheniumHCID 150194Tetrakis(dimethylsulfoxide)dichlororuthenium (II)HCID 88050071HCID 88050071, compound

Product 1

HCID 131724488HCID 131724488, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.83 g of (1R,2R)-N-(2-diphenylphosphanylbenzyl)-N′-[2-diphenylphosphanyl-5-(4-vinylbenzyloxy)benzyl]cyclohexan-1,2-diamine (3.5 mmol, 9.4% stabiliser) are refluxed for 1 hour under protective gas with 3.36 g of dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) (7 mmol) in 200 ml of absolute toluene. During the reaction, 120 mg of a yellowish solid precipitate out, which can be identified as a ruthenium-stabiliser complex. Once the reaction solution has been filtered, the solvent is removed in a rotary evaporator and the product separated by column chromatography on silica gel (isohexane/ethyl acetate 2:1). In order to isolate the product, the chromatographic fractions should not be evaporated to dryness, but instead combined with isohexane once the eluent has largely been removed. As a result, the product precipitates as a yellow/orange powder at a yield of 1.86 g (55%).

Workup

  1. filtrationOnce the reaction solution has been filtered
  2. customthe solvent is removed in a rotary evaporator
  3. customthe product separated by column chromatography on silica gel (isohexane/ethyl acetate 2:1)
  4. customIn order to isolate the product
  5. customthe chromatographic fractions should not be evaporated to dryness
  6. customhas largely been removed
  7. customAs a result, the product precipitates as a yellow/orange powder at a yield of 1.86 g (55%)

Sources & evidence

ORD record
ord-487fefd2e16b4002bed9481299488e7c
Source dataset
uspto-grants-2004_07
Patent number
US06759559B2

Reaction notes

Loading…