Pyridine → HCID 86758887, compound

HRID 1862548Notes

Reaction equation

HRID 1862548 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[N:33]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:32][C@@H:31]([CH2:39][CH2:40][OH:41])[O:30][C@H:29]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]4[O:48][CH2:49][CH2:50][O:51][C:43]=34)[C:28]=2[CH:52]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[N:33]([CH2:34][C:35]([CH3:37])([CH3:38])[CH3:36])[CH2:32][C@@H:31]([CH2:39][CH:40]=[O:41])[O:30][C@H:29]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]4[O:48][CH2:49][CH2:50][O:51][C:43]=34)[C:28]=2[CH:52]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087Triacetoxyperiodinane2×HCID 70029841HCID 70029841, compound

Product 1

HCID 86758887HCID 86758887, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (979 mg, 2.31 mmol) was added to a solution of 2-[trans-7-chloro-5-(2,3-ethylenedioxyphenyl)-1-neopentyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]-ethanol (830 mg, 1.92 mmol), pyridine (980 mL) and methylene chloride (18 mL) at 0° C. The mixture was warmed to ambient temperature and stirred 40 minutes before adding more Dess-Martin periodinane (800 mg, 1.89 mmol). After an additional 15 minutes, the reaction was quenched by addition of 5:1 saturated aqueous sodium bicarbonate/saturated aqueous sodium sulfite, stirred 5 minutes, and extracted with ether (2×). The combined organics were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (9:1 hexanes/ethyl acetate) to give 562 mg (68%) of the title compound as a white foam.

Workup

  1. waitAfter an additional 15 minutes
  2. customthe reaction was quenched by addition of 5:1 saturated aqueous sodium bicarbonate/saturated aqueous sodium sulfite
  3. stirringstirred 5 minutes
  4. extractionextracted with ether (2×)
  5. washThe combined organics were washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. custompurified by flash column chromatography (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-994c2c45f5584049a53d903e6ee045f0
Source dataset
uspto-grants-2003_03
Patent number
US06537987B1

Reaction notes

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