Pyrrolidine → 3-Pyrrolidinophenethyl Alcohol

HRID 2251891Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH2:6][O:7]C1CCCCO1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N:17]1([C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=2)[CH2:5][CH2:6][OH:7])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2-(3-bromophenethoxy)tetrahydro-2H-pyran (6.27 g, 21.9 mmol) in toluene (15 ml) and pyrrolidine (2.2 ml, 26.4 mmol) were added to a mixture of dry palladium acetate (58 mg, 0.26 mmol), 2-(di-t-butylphosphino)biphenyl (136 mg, 0.46 mmol) and sodium t-butoxide (3.23 g, 33.6 mmol), and they were stirred at 70° C. for 12 hours. Water was added to the reaction mixture. After the extraction with ethyl acetate, the product was extracted from the organic layer with 1 M hydrochloric acid. The aqueous layer was neutralized with an aqueous sodium hydroxide solution and the product was extracted with ethyl acetate. The organic layer was dried to quantitatively obtain 3-pyrrolidinophenethyl alcohol in the form of a light yellow solid.

Workup

extractionAfter the extraction with ethyl acetate
extractionthe product was extracted from the organic layer with 1 M hydrochloric acid
extractionthe product was extracted with ethyl acetate
dry with materialThe organic layer was dried to quantitatively obtain 3-pyrrolidinophenethyl alcohol in the form of a light yellow solid

Sources & evidence

ORD record: ord-84b6b3ab357f41189a2380af87a07465
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320973B2

Reaction notes

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