Triphenylphosphine → methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate

HRID 1787893Notes

Reaction equation

HRID 1787893 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([N:23]1[CH2:28][CH2:27][CH:26](O)[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].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:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH:26]2[CH2:27][CH2:28][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24][CH2:25]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 20777194Methyl 4-tert-butyl-2-hydroxybenzoate

Product 1

HCID 68532357methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of methyl 4-tert-butyl-2-hydroxybenzoate (9.45 g, 45.4 mmol), 1-Boc-piperidin-4-ol (9.6 g, 47.7 mmol) and triphenylphosphine (12.5 g, 47.7 mmol) in THF (125 mL) was added, dropwise via an addition funnel, a solution of diisopropyl azodicarboxylate (9.4 mL, 47.7 mmol) in THF (25 mL). After 72 h, the solvent was removed in vacuo and the residue was dissolved in a minimal amount of chloroform and vacuum filtered through a pad of silica gel, eluting with a solution of 20% ethyl acetate in hexanes. The filtrate was then concentrated in vacuo and the residue was chromatographed over silica gel, eluting with a gradient of 5% ethyl acetate in hexanes through 20% ethyl acetate in hexanes. The product containing fractions were combined and concentrated in vacuo to give the ether (12.9 g, 73%) as a thick colorless oil.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in a minimal amount of chloroform and vacuum
  3. filtrationfiltered through a pad of silica gel
  4. washeluting with a solution of 20% ethyl acetate in hexanes
  5. concentrationThe filtrate was then concentrated in vacuo
  6. customthe residue was chromatographed over silica gel
  7. washeluting with a gradient of 5% ethyl acetate in hexanes through 20% ethyl acetate in hexanes
  8. additionThe product containing fractions
  9. concentrationconcentrated in vacuo
  10. customto give the ether (12.9 g, 73%) as a thick colorless oil

Sources & evidence

ORD record
ord-503ed7f5676548619595cdfb9337a1fe
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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