Potassium Hydroxide → HCID 68955963, compound

HRID 1971268Notes

Reaction equation

HRID 1971268 reaction equation
S1C=CC(C=O)=C1.[OH-].[K+].[N+:10]([CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])#[C-:11].[S:20]1[CH:24]=[CH:23][C:22]([C@@H:25]2[O:29][CH:28]=[N:27][C@H:26]2[C:30]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])=[CH:21]1>CO.C(OCC)(=O)C>[S:20]1[CH:24]=[CH:23][C:22]([C@@H:25]2[O:29][CH:28]=[N:27][C@H:26]2[C:30]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])=[CH:21]1.[N:27]1[CH:24]=[CH:23][CH:22]=[CH:25][C:26]=1[C@@H:30]1[O:31][CH:11]=[N:10][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14]

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-HCID 68953618HCID 68953618, compound

Product 2

HCID 68953618HCID 68953618, compoundHCID 68955963HCID 68955963, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

BLE 04124A was prepared in accordance with method D using thiophen-3-carboxaldehyde (0.475 mL, 5.42 mmol), KOH (0.276 mg, 4.92 mmol) in methanol (5 mL) and 2-isocyano-1-(pyrrolidin-1-yl)ethanone BLE 04098 (0.75 g, 5.43 mmol). After work-up the residue obtained was recristallized from ethyl acetate to obtain after filtration trans-(4,5-dihydro-5-(thiophen-3-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanone BLE 04110A as a yellow pale solid (0.498 g, 40% yield).

Workup

  1. customAfter work-up the residue obtained
  2. customto obtain

Sources & evidence

ORD record
ord-d97cb6d299464594a281f46086b84aed
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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