3-Hydroxypyridine → HCID 67154758, compound

HRID 1027939Notes

Reaction equation

HRID 1027939 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH:44]([CH2:45][OH:46])[CH2:43][CH:42]2[CH:40]1[CH2:41]2)=[O:38])([CH3:35])([CH3:34])[CH3:33].O[C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1>O1CCCC1>[C:32]([O:36][C:37]([N:39]1[CH:44]([CH2:45][O:46][C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)[CH2:43][CH:42]2[CH:40]1[CH2:41]2)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66981875HCID 66981875, compound

Product 1

HCID 67154758HCID 67154758, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To an ice cold solution of triphenylphosphine (1.66 grams, 6.4 mmol) in dry tetrahydrofuran (7 mL) was added diethyl azodicarboxylate (1.0 mL, 6.4 mmol). The mixture was warmed to room temperature and stirred for 30 minutes. The reaction mixture was cooled to 0° C. and a solution of 3-Hydroxymethyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (obtained in step (vii) of preparation 1) (0.9 grams, 4.2 mmol) in dry tetrahydrofuran (7 mL) was added followed by a solution of 3-hydroxypyridine (0.6 grams, 6.4 mmol) in dry tetrahydrofuran (14 mL). The reaction mixture was gradually warmed to room temperature and stirred for 0.16 hours. The volatiles were evaporated under reduced pressure and crude obtained was purified by flash column chromatography using 230-400 mesh silica gel to obtain title compound 0.83 grams as gummy liquid. Yield: 68%.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureThe reaction mixture was gradually warmed to room temperature
  3. stirringstirred for 0.16 hours
  4. customThe volatiles were evaporated under reduced pressure and crude
  5. customobtained
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-bea0d19a4d644befa663ba4b60846aab
Source dataset
uspto-grants-2014_05
Patent number
US08735423B2

Reaction notes

Loading…