Triphenylphosphine → HCID 118098695, compound

HRID 708827Notes

Reaction equation

HRID 708827 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[SH:34][C:35]1[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][C:36]=1[CH2:37][N:38]([CH3:49])[C:39](=[O:48])[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[CH3:57][O:58][CH2:59][C@H:60](O)[CH3:61]>C1COCC1>[CH3:57][O:58][CH2:59][C@@H:60]([S:34][C:35]1[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][C:36]=1[CH2:37][N:38]([CH3:49])[C:39](=[O:48])[O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH3:61]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733589(R)-(-)-1-Methoxy-2-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 118098694HCID 118098694, compound

Product 1

HCID 118098695HCID 118098695, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (355 mg, 1.354 mmol) in THF (4 mL) at 0° C., was added DIAD (0.263 mL, 1.354 mmol) dropwise. The mixture was stirred at 0° C. for 10 min affording a colorless suspension. A solution of 6B (300 mg, 0.903 mmol) and (R)-1-methoxypropan-2-ol (0.133 mL, 1.354 mmol) in THF (2 mL) was added dropwise. The resultant dark red solution was stirred at 0° C. for 0.5 h, then was allowed to slowly warm to rt over night. The reaction mixture was concentrated. The crude product was purified by flash chromatography (loaded in chloroform onto a 40 g column and eluted with a gradient from 0 to 40% ethyl acetate/hexanes) to afford 6C (396 mg, 108% yield) as yellow oil/semi-solid. MS (ESI) m/z: 405.2 [M+1]+; 1H NMR (400 MHz, chloroform-d) δ ppm 8.07 (d, J=8.53 Hz, 1H) 7.96 (d, J=18.57 Hz, 1H) 7.32-7.51 (m, 6H) 5.11-5.26 (m, 2H) 4.59 (d, J=18.07 Hz, 2H) 3.58-3.68 (m, 1H) 3.47 (d, J=6.53 Hz, 2H) 3.37 (s, 3H) 2.99 (br. s., 3H) 1.40 (br. s., 3H).

Workup

  1. customaffording a colorless suspension
  2. stirringThe resultant dark red solution was stirred at 0° C. for 0.5 h
  3. temperatureto slowly warm to rt over night
  4. concentrationThe reaction mixture was concentrated
  5. customThe crude product was purified by flash chromatography (
  6. washeluted with a gradient from 0 to 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9c3b2d80c74c412c88f881cb1ad733f1
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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