Triphenylphosphine → ethyl ((1S)-5-{3-[(5-cyano-2-pyridinyl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235916Notes

Reaction equation

HRID 2235916 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1.[CH2:14]([O:16][C:17](=[O:29])[CH2:18][C@H:19]1[C:27]2[C:22](=[CH:23][C:24](O)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:1][C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][CH:25]=2)[C@H:19]([CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:29])[CH2:20][CH2:21]3)=[N:7][CH:8]=1)#[N:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 431521396-(3-Hydroxypropoxy)nicotinonitrile

Product 1

HCID 59300525ethyl ((1S)-5-{3-[(5-cyano-2-pyridinyl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3-hydroxypropoxy)nicotinonitrile (Example 257) (0.86 g, 4.83 mmol) and ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 0.89 g, 4.02 mmol) in THF (20 mL) was added triphenylphosphine (1.49 g, 5.63 mmol) and 1,1′-(azodicarbonyl)-dipiperidine (1.44 g, 5.63 mmol) under argon. The golden yellow mixture was stirred at rt for 18 h and concentrated under reduced pressure. The product (1.22 g, 80%) was isolated after purification by silica gel flash chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 8.47 (dd, 1H), 7.79 (dd, 1H), 7.05 (d, 1H), 6.82 (d, 1H), 6.77 (d, 1H), 6.69 (dd, 1H), 4.56 (t, 2H), 4.16 (q, 2H), 4.11 (t, 2H), 3.51 (qt, 1H), 2.95-2.78 (m, 2H), 2.70 (dd, 1H), 2.44-2.32 (m, 2H), 2.30-2.20 (m, 2H), 1.80-1.70 (m, 1H), 1.28 (t, 3H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb171170241b46adbf41b3fc09c18b44
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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