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Cesium carbonate → trans-N-cyanomethyl-2-(4-hydroxymethyl-phenylsulfanylmethyl)-cyclohexanecarboxamide

HRID 2222942
Notes
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Reaction equation

HRID 2222942 reaction equation
[F-].[Cs+].C(=O)([O-])[O-].[Cs+].[Cs+].C([Si]([S:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=1)(C(C)C)C(C)C)(C)C.[C:28]([CH2:30][NH:31][C:32]([C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:40]Br)=[O:33])#[N:29]>CN(C)C=O.ClCCl>[C:28]([CH2:30][NH:31][C:32]([C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:40][S:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][OH:27])=[CH:24][CH:25]=1)=[O:33])#[N:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 69114972(4-Triisopropylsilanylsulfanyl-phenyl)-methanolHCID 86596125trans-2-Bromomethyl-N-cyanomethylcyclohexanecarboxamide

Product 1

HCID 86596157trans-N-cyanomethyl-2-(4-hydroxymethyl-phenylsulfanylmethyl)-cyclohexanecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Cesium fluoride (0.829 g, 5.46 mmol) and cesium carbonate (0.456 g, 1.4 mmol) were added to a stirred solution of (4-triisopropylsilanylsulfanyl-phenyl)-methanol (0.808 g, 2.73 mmol) and trans-2-bromomethyl-cyclohexanecarboxylic acid cyanomethyl amide (0.906 g, 3.50 mmol) in dry dimethylformamide (910 mL). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was diluted with dichloromethane and washed with 1N HCl, then with saturated aqueous sodium bicarbonate. The organic layer was dried with magnesium sulfate, filtered, and concentrated by rotary evaporation to yield trans-N-cyanomethyl-2-(4-hydroxymethyl-phenylsulfanylmethyl)-cyclohexanecarboxamide as a white solid that was carried forward without further purification.

Workup

  1. washwashed with 1N HCl
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6b2a4f8837f44639bff10ff2221a7f90
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07371747B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes