Triphenylphosphine → HCID 117667237, compound

HRID 712719Notes

Reaction equation

HRID 712719 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:34][C:35]1[CH:36]=[C:37]([OH:41])[CH:38]=[N:39][CH:40]=1.[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH2:52][C@H:51](O)[CH2:50]1)=[O:48])([CH3:45])([CH3:44])[CH3:43]>C1COCC1>[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH2:52][C@@H:51]([O:41][C:37]2[CH:38]=[N:39][CH:40]=[C:35]([Br:34])[CH:36]=2)[CH2:50]1)=[O:48])([CH3:45])([CH3:43])[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 117667237HCID 117667237, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of PPh3 (1.2 g, 4.5 mmol) in THF (50 mL) is added DIAD (0.81 mL, 4.1 mmol), dropwise. After stirring at 0° C. for 15 min, 5-bromo-pyridin-3-ol (441 mg, 2.5 mmol) and (S)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.5 mmol) are added and the mixture is warmed and stirred at room temperature for 16 h. The mixture is concentrated and purified by flash column chromatography to give 596 mg of (R)-3-(5-bromo-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperaturethe mixture is warmed
  2. stirringstirred at room temperature for 16 h
  3. concentrationThe mixture is concentrated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-ca57909b744d4f82945c95547dc5f47c
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…