Triphenyl phosphite → HCID 66787018, compound

HRID 1096627Notes

Reaction equation

HRID 1096627 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23](O)=O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1(OP(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1>N1C=CC=CC=1>[CH3:1][C:2]1[C:3]2[N:9]=[C:23]([C@@H:19]3[CH2:20][CH2:21][CH2:22][N:17]([C:15]([O:14][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:16])[CH2:18]3)[NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7540Triphenyl phosphiteHCID 175932,3-DiaminotolueneHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 66787018HCID 66787018, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a microwave vial was added 3-methylbenzene-1,2-diamine (150 mg, 1.23 mmol) and (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (281 mg, 1.23 mmol). The mixture was dissolved with pyridine (6.2 mL). Triphenylphosphite (469 mg, 1.51 mmol) was added and the vial was capped. The reaction was microwaved at 220° C. for 10 minutes. Solvent was removed under vacuum and the residue was purified by preparatory LC/MS (20-30% CH3CN in H2O) to give (R)-tert-butyl 3-(4-methyl-1H-benzo[d]imidazol-2-yl)piperidine-1-carb oxylate (39A) (80 mg, 21% yield). ESI-MS:m/z 316.4 (M+H)+.

Workup

  1. customthe vial was capped
  2. customThe reaction was microwaved at 220° C. for 10 minutes
  3. customSolvent was removed under vacuum
  4. customthe residue was purified by preparatory LC/MS (20-30% CH3CN in H2O)

Sources & evidence

ORD record
ord-687fc4b93d794911911a74b0d9c38c08
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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