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

HRID 2108729Notes

Reaction equation

HRID 2108729 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]([CH2:26][CH2:27][CH2:28]O)[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 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-hydroxyphenylacetate (0.409 g, 2.4 mmol), 3-(N-Boc-piperidin-4-yl)-propan-1-ol (0.50 g, 20.5 mmol) and triphenylphosphine (0.645, 24.6 mmol) in THF, 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 and the residue was dissolved in methylene chloride (2 mL) and loaded on a silica gel column. The product was eluted with 20% ethyl acetate in hexane, to afford methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate (0.5 g, 62%). 1H NMR (500 MHz, CDCl3) 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
  3. dissolutionthe residue was dissolved in methylene chloride (2 mL)
  4. washThe product was eluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-89bf11d8bdfd40db971a72f294fbb3e8
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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