3-(2-Methoxyphenyl)pyrrolidine → 1-(1.4-Dioxaspiro[4.5]dec-8-ylmethyl)-3-(2-methoxyphenyl)pyrrolidine

HRID 1743754Notes

Reaction equation

HRID 1743754 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1.Br[CH2:15][CH:16]1[CH2:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18][CH2:17]1>O1CCOCC1.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>[O:20]1[C:19]2([CH2:24][CH2:25][CH:16]([CH2:15][N:11]3[CH2:12][CH2:13][CH:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:10]3)[CH2:17][CH2:18]2)[O:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 150299633-(2-Methoxyphenyl)pyrrolidineHCID 222365708-(Bromomethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 222365691-(1.4-Dioxaspiro[4.5]dec-8-ylmethyl)-3-(2-methoxyphenyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 1859152-NaphthylalanineSolvent

Procedure

1 g of 3-(2-Methoxyphenyl)pyrrolidine is dissolved in 60 ml of dioxane and 0.85 g Nal, followed by 1.2 ml of N,N-ethyldiisopropylamine and 1.5 g of 8-bromomethyl-1.4-dioxaspiro[4.5]decane, dissolved in 5 ml of dioxane, are added. The reaction mixture is stirred overnight at 80°, evaporated and the residue extracted with ethylacetate/2N Na2CO3, followed by aqueous NaCl. The combined, dried and evaporated organic phases yields an oily residue which is purified by flash chromatography on silica gel using t-butylmethylether as a solvent system providing the product as an oil. MS (EI): M+=331; NMR (DMSO): 1.1 (2H, m), 1.45 (3H, m), 1.6-1.8 (5H, m), 2.15 (1H, m), 2.25 (2H, m), 2.4 (1H, t), 2.6 (2H, m), 2.8 (1H, t), 3.6 (1H, t), 3.75 (3H, s), 3.85 (4H, s), 6.9 (2H, dd), 7.15 (1H, t), 7.3 (1H, d).

Workup

  1. additionare added
  2. customevaporated
  3. extractionthe residue extracted with ethylacetate/2N Na2CO3
  4. customdried
  5. customevaporated organic phases
  6. customyields an oily residue which
  7. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-921c6d0112b64f239809152970731724
Source dataset
uspto-grants-2006_03
Patent number
US07012085B2

Reaction notes

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