Piperidine → 3-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

HRID 480687Notes

Reaction equation

HRID 480687 reaction equation
C([O:4][C:5]([CH2:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:6])C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCCC1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([O:15][C:13]([C:12]([CH3:21])([O:11][C:10]1[CH:9]=[C:8]([CH2:7][C:5]([OH:6])=[O:4])[CH:24]=[CH:23][CH:22]=1)[CH3:20])=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 18766493tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

Product 1

HCID 187664143-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-[3-(allyloxycarbonylmethyl)phenoxy]-2-methylpropionate (1.63 g, 4.42 mmol) was dissolved in tetrahydrofuran (40 mL). Subsequently, tetrakis(triphenylphosphine)palladium (508 mg, 0.44 mmol), triphenylphosphine (346 mg, 1.32 mmol), and piperidine (8.74 mL, 88.4 mmol) were added thereto, and the mixture was stirred for two hours at room temperature. The resultant mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol/acetic acid=50/1/0.2), whereby the target compound was obtained (1.45 g, 4.42 mmol, q).

Workup

  1. concentrationThe resultant mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol/acetic acid=50/1/0.2), whereby the target compound
  2. customwas obtained (1.45 g, 4.42 mmol, q)

Sources & evidence

ORD record
ord-67ade632f52544c69b722531dc08b074
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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