1-Phenylethanol, (S)- → HCID 68681142, compound

HRID 1820442Notes

Reaction equation

HRID 1820442 reaction equation
[Cl-].C(C[P+](C)(C)C)#N.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:19]1([C@@H:25](O)[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[F:28][C:29]1([F:57])[CH2:34][CH2:33][N:32]([C:35]([C:37]2[NH:38][C:39]3[C:44]([CH:45]=2)=[CH:43][C:42]([C:46]([N:48]2[CH2:53][CH2:52][N:51]([CH:54]([CH3:56])[CH3:55])[CH2:50][CH2:49]2)=[O:47])=[CH:41][CH:40]=3)=[O:36])[CH2:31][CH2:30]1>C1(C)C=CC=CC=1>[F:57][C:29]1([F:28])[CH2:34][CH2:33][N:32]([C:35]([C:37]2[N:38]([C@H:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:26])[C:39]3[C:44]([CH:45]=2)=[CH:43][C:42]([C:46]([N:48]2[CH2:49][CH2:50][N:51]([CH:54]([CH3:55])[CH3:56])[CH2:52][CH2:53]2)=[O:47])=[CH:41][CH:40]=3)=[O:36])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 4431351-Phenylethanol, (S)-HCID 3251421Potassium bis(trimethylsilyl)amideHCID 57431663(Cyanomethyl)trimethylphosphonium chlorideHCID 68680853(4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 68681142HCID 68681142, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Example 123 was independently synthesized according to example 74 under inversion of the configuration (e.e. >94%), from (cyanomethyl)trimethylphosphonium chloride (prepared according to Tetrahedron Lett. 1996, 37 (14), 2459-62), potassium bis(trimethylsilyl)amide, (S)-1-phenylethanol and (4,4-difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 32) in toluene, to give the compound as a light brown foam (32%).

Workup

  1. customExample 123 was independently synthesized

Sources & evidence

ORD record
ord-db782720fd0246bf8a07594e99388b73
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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