Tributylphosphine → N-Boc-3-(2-piperidin-4-yl-ethoxy)-benzoic acid ethyl ester

HRID 1401136Notes

Reaction equation

HRID 1401136 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH2:24]([O:23][C:21](=[O:22])[C:20]1[CH:26]=[CH:27][CH:28]=[C:18]([O:16][CH2:15][CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[CH:19]=1)[CH3:25]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 24522Ethyl 3-hydroxybenzoateHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 66930054N-Boc-3-(2-piperidin-4-yl-ethoxy)-benzoic acid ethyl esterYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

N-Boc-4-piperidine ethanol (15 g, 65 mmol) and ethyl 3-hydroxybenzoate (11 g, 65 mmol) were dissolved in dry THF (750 ml) under N2. To this was added tri-n-butylphosphin (24 ml, 98 mmol) and ADDP (25 g, 98 mmol) resulting in a suspension, which was stirred overnight at 20° C. The mixture was concentrated in vacuo to ˜100 ml, filtered, and the filtrate was evaporated with silica gel. Flash chromatography (EtOAc/heptane 1:4) afforded 24 g of the title compound. LC-MS (m/z): 401 (M+23).

Workup

  1. customresulting in a suspension, which
  2. concentrationThe mixture was concentrated in vacuo to ˜100 ml
  3. filtrationfiltered
  4. customthe filtrate was evaporated with silica gel

Sources & evidence

ORD record
ord-c55cce2106a445f8bc09ca0263e6649b
Source dataset
uspto-grants-2014_12
Patent number
US08907096B2

Reaction notes

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