Pyridine → HCID 86696716, compound

HRID 2365861Notes

Reaction equation

HRID 2365861 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.O[CH:13]1[CH2:17][CH:16]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:15]([CH2:29][OH:30])[CH2:14]1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH:13]12[CH2:14][CH:15]([CH:16]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:17]1)[CH2:29][O:30]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 86696715HCID 86696715, compound

Product 1

HCID 86696716HCID 86696716, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of TsCl (290 mg, 1.52 mmol) in dry toluene (3.0 mL) was added dropwise to a solution of benzyl 4-hydroxy-2-(hydroxymethyl)cyclopentylcarbamate (100 mg, 0.380 mmol) and dry pyridine (3.0 mL) in dry toluene (6.0 mL) at 0° C. The mixture was then warmed to room temperature and stirred for 2 days. The reaction mixture was heated to 120° C. and stirred for another 16 hours. After concentration, the residue was purified by reverse phase Combi-flash (0.3% NH4HCO3/CH3CN) to afford benzyl 2-oxa-bicyclo[2.2.1]heptan-5-ylcarbamate as a solid (58 mg, 62% yield). 1H NMR (500 MHz, CD3OD) δ 7.37-7.31 (m, 5H), 5.09 (s, 2H), 4.33 (s, 1H), 3.73 (d, J=5.5 Hz, 1H), 3.63-3.61 (m, 1H), 3.48 (d, J=7.5 Hz, 1H), 2.53 (s, 1H), 2.07-2.04 (m, 1H), 1.72 (d, J=10.5 Hz, 1H), 1.61 (d, J=11.0 Hz, 1H), 1.42 (d, J=14.0 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was heated to 120° C.
  2. stirringstirred for another 16 hours
  3. concentrationAfter concentration
  4. customthe residue was purified by reverse phase Combi-flash (0.3% NH4HCO3/CH3CN)

Sources & evidence

ORD record
ord-9caefc01c5924754b5ae8c5fcba2a534
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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