Benzyl Alcohol → HCID 67206080, compound

HRID 1593640Notes

Reaction equation

HRID 1593640 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][C@@H:7](C(O)=O)[CH2:6][C:5]2=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][C@@H:7]([NH:37][C:40](=[O:25])[O:49][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:6][C:5]2=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69233329HCID 69233329, compound

Product 1

HCID 67206080HCID 67206080, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (3R)-6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (0.60 g, 2.57 mmol) in anhydrous 1,4-dioxane (20 mL) was added diphenylphosphorylazide (0.7 mL, 3.24 mmol), triethylamine (0.39 mL, 2.83 mmol), and 4 A molecular sieves. After stirring at room temperature for 2 h, benzyl alcohol (0.8 mL, 7.71 mmol) was added and the reaction was heated at 70° C. for 2 h. After cooling, the mixture was filtered and the filtrate was concentrated in vacuo. Purification by chromatography on silica gel afforded 340 mg of the title compound as a colorless oil.

Workup

  1. temperaturethe reaction was heated at 70° C. for 2 h
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-b77da451bda945abbc8abcc97044b55a
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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