Triphenylphosphine → HCID 67460302, compound

HRID 554553Notes

Reaction equation

HRID 554553 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH:15]1([C:18]2[CH:23]=[CH:22][C:21]([C:24]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[OH:32])=[O:25])=[CH:20][CH:19]=2)[CH2:17][CH2:16]1.[CH2:33]([O:40][C@@H:41]1[C@@H:46]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@H:45]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@@H:44]([CH2:63][O:64][CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH2:43][C@@H:42]1O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH:15]1([C:18]2[CH:19]=[CH:20][C:21]([C:24]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][C:27]=3[O:32][C@@H:42]3[CH2:43][C@H:44]([CH2:63][O:64][CH2:65][C:66]4[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=4)[C@@H:45]([O:55][CH2:56][C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C@H:46]([O:47][CH2:48][C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[C@H:41]3[O:40][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:25])=[CH:22][CH:23]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11226475HCID 11226475, compoundHCID 23103592HCID 23103592, compound

Product 1

HCID 67460302HCID 67460302, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a nitrogen stream, diisopropylazodicarboxylate (0.14 mL, 0.72 mmol) was slowly added dropwise to a mixture of (4-cyclopropylphenyl)-(3-hydroxypyridin-4-yl)methanone (0.18 g, 0.74 mmol), (1S,2S,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethylcyclohexanol (0.20 g, 0.37 mmol), triphenylphosphine (0.19 g, 0.74 mmol) and toluene (1.3 mL) under cooling with ice. The reaction mixture was stirred at room temperature for three hours, and then the solvent was distilled under reduced pressure and the obtained residue was purified by silica gel flash column chromatography [developing solution=n-hexane:ethyl acetate (2:3)] to obtain the title product (0.20 g, 71%).

Workup

  1. temperatureunder cooling with ice
  2. distillationthe solvent was distilled under reduced pressure
  3. customthe obtained residue was purified by silica gel flash column chromatography [developing solution=n-hexane:ethyl acetate (2:3)]

Sources & evidence

ORD record
ord-3ee55ca2575b488fa36912da59841eec
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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