2-[2-(3-Hydroxy-propenyl)-benzofuran-3-ylmethyl]-pyrrolidine-1-carboxylic acid benzyl ester → 3-(3-Pyrrolidin-2-ylmethyl-benzofuran-2-yl)-propan-1-ol

HRID 1054014Notes

Reaction equation

HRID 1054014 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[CH:26]=[CH:27][CH2:28][OH:29])=O)C1C=CC=CC=1>CO>[NH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[CH2:26][CH2:27][CH2:28][OH:29]

Participants

3

Reactant 1

HCID 671480522-[2-(3-Hydroxy-propenyl)-benzofuran-3-ylmethyl]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 671485293-(3-Pyrrolidin-2-ylmethyl-benzofuran-2-yl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 60 (1.1 g, 2.8 mmol) and 10% Pd-on-carbon (1 g) in MeOH (40 mL) was placed under an atmosphere of hydrogen gas (45 PSI) and shaken for 2 h using a Parr apparatus. The catalyst was removed by filtration through a bed of celite and the clarified filtrate was concentrated in vacuo to afford 725 mg (quant.) of 61 as a yellow oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ7.47-7.36 (m, 2H), 7.21-7.17 (m, 2H), 4.59 (br s, 2H), 3.57-3.50 (m, 2H), 3.40-3.31 (m, 1H), 3.08-2.94 (m, 1H), 2.89-2.69 (m, 2H), 2.05-1.95 (m, 2H), 1.93-1.49 (m, 2H) ppm.

Workup

  1. customThe catalyst was removed by filtration through a bed of celite
  2. concentrationthe clarified filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e2f63fb14cab4c509c37a69d9540e9b0
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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