Pyridine → HCID 57920207, compound

HRID 2098380Notes

Reaction equation

HRID 2098380 reaction equation
[CH2:1]([C:8]1([C:21](=[O:35])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])[CH:24]=2)[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1(C(O)=O)CC[N:46]([C:49](OC(C)(C)C)=O)CC1)C1C=CC=CC=1.[N:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.C(Cl)(=O)C(Cl)=O.C[N:72](C)C(=O)OC1C=CC=C(N)C=1>CN(C=O)C.C(Cl)Cl>[CH3:33][N:31]([CH3:32])[C:30](=[O:34])[O:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([NH:22][C:21]([C:8]2([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10][N:11]([C:14]3[C:63]4[C:61]([CH3:62])=[CH:60][NH:59][C:64]=4[N:72]=[CH:49][N:46]=3)[CH2:12][CH2:13]2)=[O:35])[CH:24]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 298773-Aminophenyl dimethylcarbamateHCID 65578Oxalyl chlorideHCID 121510204-Benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acidHCID 67036789HCID 67036789, compound

Product 1

HCID 57920207HCID 57920207, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Preparation of tert-butyl 4-benzyl-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate. Under an atmosphere of N2, 4-benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (0.2 g, 0.626 mmol), pyridine (0.202 mL, 2.5 mmol), and DMF (3 drops) were dissolved in CH2Cl2 (10 mL) and cooled in an ice bath. To the cooled solution, oxalyl chloride (0.06 mL, 0.688 mmol) was added dropwise. The reaction was then removed from the ice bath and stirred at room temperature for 30 min. The reaction was re-cooled in an ice bath, and 3-aminophenyl dimethylcarbamate (0.112 g, 0.626 mmol) was added in one portion. The reaction was stirred overnight, and then washed with 1 N aq. HCl and brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (ethyl acetate:hexanes gradient) to give the title compound in 54% yield. MS (ES+) [M+NH4]+=500.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction was then removed from the ice bath
  3. temperatureThe reaction was re-cooled in an ice bath
  4. stirringThe reaction was stirred overnight
  5. washwashed with 1 N aq. HCl and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography (ethyl acetate:hexanes gradient)

Sources & evidence

ORD record
ord-4a87cd720b6c462da641ae6d39203c8a
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Reaction notes

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