Benzyl Alcohol → HCID 86707712, compound

HRID 1408964Notes

Reaction equation

HRID 1408964 reaction equation
C([N:3]([CH2:6]C)[CH2:4][CH3:5])C.[CH3:8][O:9][C:10]([C@@:12]1([CH3:22])[CH2:16]C[C@@H](C(O)=O)[C:13]1([CH3:21])[CH3:20])=[O:11].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[CH2:40]([O:47][C:6]([NH:3][C@@H:4]1[CH2:5][CH2:22][C@:12]([CH3:16])([C:10]([O:9][CH3:8])=[O:11])[C:13]1([CH3:20])[CH3:21])=[O:30])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 7366661400689-82-8

Product 1

HCID 86707712HCID 86707712, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.795 ml, 12.88 mmol) was added dropwise to a solution of (1R,3S)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid (1.84 g, 8.59 mmol) in toluene (22.08 ml) and THF (2.454 ml), followed by addition of diphenylphosphoryl azide (2.221 ml, 10.31 mmol). The reaction was stirred at room temperature for 1.5 hours. Benzyl alcohol (1.339 ml, 12.88 mmol) was added. The reaction was heated at 110° C. for 6 hrs. The reaction was cooled to room temperature and diluted with ethyl acetate. The solution was washed successively with (sat.) sodium bicarbonate, water, and (sat.) sodium chloride. The organic extract was dried with sodium sulfate, filtered, and concentrated under reduced pressure to give an orange oil. The crude product was chromatographed on the silica gel column eluted with 0-50% ethyl acetate in hexane to afford the title compound (1.74 g, 5.45 mmol, 63.4% yield) as a colorless oil. LC/MS found [M+H]+=320.1. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.39-7.27 (m, 5H), 5.15-5.01 (m, 2H), 4.14-4.02 (m, 1H), 3.70-3.62 (m, 3H), 2.53-2.40 (m, 1H), 2.20-2.08 (m, 1H), 1.51-1.40 (m, 2H), 1.22-1.19 (m, 3H), 1.05 (s, 3H), 0.73 (s, 3H).

Workup

  1. temperatureThe reaction was heated at 110° C. for 6 hrs
  2. temperatureThe reaction was cooled to room temperature
  3. washThe solution was washed successively with (sat.) sodium bicarbonate, water, and (sat.) sodium chloride
  4. extractionThe organic extract
  5. dry with materialwas dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an orange oil
  9. customThe crude product was chromatographed on the silica gel column
  10. washeluted with 0-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-becaa210a67442e9976e9306ac6f8584
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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