Triphenylphosphine → Ethyl{(1S)-5-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetate

HRID 46033Notes

Reaction equation

HRID 46033 reaction equation
C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:38]([O:40][C:41](=[O:53])[CH2:42][C@H:43]1[C:51]2[C:46](=[CH:47][C:48]([OH:52])=[CH:49][CH:50]=2)[CH2:45][CH2:44]1)[CH3:39].[CH3:54][C:55]1[N:56]=[C:57]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[O:58][C:59]=1[CH2:60][CH2:61]O>C1COCC1.C(Cl)Cl>[CH3:54][C:55]1[N:56]=[C:57]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[O:58][C:59]=1[CH2:60][CH2:61][O:52][C:48]1[CH:47]=[C:46]2[C:51](=[CH:50][CH:49]=1)[C@H:43]([CH2:42][C:41]([O:40][CH2:38][CH3:39])=[O:53])[CH2:44][CH2:45]2

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 219427522-(4-Methyl-2-phenyl-1,3-oxazol-5-yl)ethanol

Product 1

HCID 60128085Ethyl{(1S)-5-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetateYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

ADDP (0.205 g, 0.81 mmol) was added to a mixture of PPh3 (0.212 g, 0.81 mmol), ethyl[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (0.107 g, 0.49 mmol), and 2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethanol (step 4, Example 51, 0.110 g, 0.54 mmol) in THF (5 mL). The reaction was stirred overnight at rt, and additional ADDP (0.136 g, 0.54 mmol) and PPh3 (0.141 g, 0.54 mmol) were added with CH2Cl2 (5 mL). The solution was stirred for 24 hours at rt and filtered. The filtrate was evaporated and the resulting mixture was purified by Biotage using a gradient 0 to 50%. EtOAc/hexane. Gave ethyl {(1S)-5-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetate (0.145 g, 66% yield) as yellowish oil. ES-MS m/z 406.2 ((MH)+); HPLC RT (min.) 3.89; 1H NMR (Acetone-d6) δ 7.85-7.82 (m, 2H), 7.36-7.30 (m, 3H), 6.94 (d, 1H), 6.65 (s, 1H), 6.60-6.55 (m, 1H), 4.10 (t, 2H), 3.98 (q, 2H), 3.31-3.27 (m, 1H), 3.03 (t, 2H), 3.27-2.51 (m, 3H), 2.24-2.14 (m, 2H), 2.18 (s, 3H), 1.58-1.53 (m, 1H), 1.08 (t, 3H).

Workup

  1. stirringThe solution was stirred for 24 hours at rt
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe resulting mixture was purified by Biotage

Sources & evidence

ORD record
ord-a4546baa493c43e18eca7a9d89b25d83
Source dataset
uspto-grants-2013_09
Patent number
US08541618B2

Reaction notes

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