Triphenylphosphine → Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate

HRID 2108715Notes

Reaction equation

HRID 2108715 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH:26](O)[CH2:27][CH3:28])[CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:13]([N:20]1[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][CH2:28][O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH2:24][CH2:25]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 39129Methyl 3-HydroxyphenylacetateHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 17788070N-Boc-piperidin-4-yl-propanol

Product 1

HCID 21071299Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetateYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To THF solution of 0.409 g (2.4 mmol) methyl 3-hydroxyphenylacetate, 0.50 g (20.5 mmol) N-Boc-piperidin-4-yl-propanol and 0.645 g (24.6 mmol) triphenylphosphine was added diisopropyl azodicarboxylate at 0° C. slowly, then the ice bath was removed and the reaction mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation, the residue was dissolved in 2 mL methylene chloride and was loaded on a silica gel column and, the product eluted with 80% hexane and 20% ethyl acetate. Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate (0.5 g, 62%) was obtained. 1H NMR (500 MHz, CDCl3) δ 1.1 (m, 2H), 1.4 (m, 2H), 1.46 (s, 9H), 1.66 (d, 2H), 1.78(m, 2H), 2.67 (t, 2H), 3.58 (s, 2H), 3.68 (s, 3H), 4.05 (m, 2H), 6.75 (m, 3H), 7.18 (dd, 1H).

Workup

  1. customthe ice bath was removed
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue was dissolved in 2 mL methylene chloride
  4. washthe product eluted with 80% hexane and 20% ethyl acetate

Sources & evidence

ORD record
ord-65b51a94c994419c9ac58300d363f8b2
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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