Triphenylphosphine → ethyl{(1S)-5-[2-(6-chloro-2-pyridinyl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetate

HRID 2235968Notes

Reaction equation

HRID 2235968 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:26])[CH2:15][C@H:16]1[C:24]2[C:19](=[CH:20][C:21](O)=[CH:22][CH:23]=2)[CH2:18][CH2:17]1)[CH3:12].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:11]([O:13][C:14](=[O:26])[CH2:15][C@H:16]1[C:24]2[C:19](=[CH:20][C:21]([O:10][CH2:9][CH2:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17]1)[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 189285562-(6-Chloropyridin-2-yl)ethanol

Product 1

HCID 59300493ethyl{(1S)-5-[2-(6-chloro-2-pyridinyl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetateYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-6-chloro-2-pyridinyl)ethanol (Example 470, 250 mg, 1.59 mmol) and ethyl[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 698 mg, 3.17 mmol) in THF (4 mL) were added PPh3 (832 mg, 3.17 mmol) and DIAD (641 mg, 3.17 mmol). The reaction mixture was vigorously stirred at rt for 24 h, concentrated under reduced pressure, and the residue was purified by silica gel chromatography (6:1 hexanes/EtOAc) to give the product (170 mg, 30%). 1H NMR (400 MHz, CDCl3) δ 1.28 (t, 3H), 1.72-1.77 (m, 1H), 2.34-2.43 (m, 2H), 2.71 (dd, 1H), 2.81-2.89 (m, 2H), 3.21 (t, 2H), 3.51-3.52 (m, 1H), 4.17 (q, 2H), 4.31 (t, 2H), 6.69 (d, 1H), 6.76 (s, 1H), 7.04 (d, 1H), 7.19 (dd, 2H), 7.57 (t, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (6:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-99ee738095434fddbddfa4992b58dedc
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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