HCID 13320303, compound → (3R,4R)-1-Methyl-4-phenoxypyrrolidin-3-ol

HRID 1381217Notes

Reaction equation

[I-].[OH:2][C@H:3]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][N+:5](C)([CH2:15]C2C=CC=CC=2)[CH2:4]1>[Ag]=O.C(O)C>[CH3:15][N:5]1[CH2:6][C@@H:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:3]([OH:2])[CH2:4]1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 9.3 g. (22.6 mmol.) of trans-3-hydroxy-1-methyl-4-phenoxy-1-phenylmethylpyrrolidinium iodide in 200 ml. of absolute ethanol and 100 ml. of 190 ethanol was stirred at ambient temperature for 0.5 hr. with 2.6 g. (11.3 mmol.) of silver oxide. After 0.2 g. more silver oxide was added, the mixture was warmed to 45° C. and stirred for an additional 15 min. The mixture was separated by filtration through Celite, and the volume of the filtrate was reduced to 200 ml. This solution was treated with ca. 0.5 g. of 10% Pd/C catalyst and was shaken with H2 in the Parr reduction apparatus for 3 hr. The suspension was filtered through Celite and the filtrate was concentrated to give 4.3 g. of crystalline solid. This material, when recrystallized from cyclohexane, gave 3.66 g. (84%) of off-white crystals, m.p. 89.0°-90.0° C.

Workup

customThe mixture was separated by filtration through Celite
additionThis solution was treated with ca. 0.5 g
stirringof 10% Pd/C catalyst and was shaken with H2 in the Parr reduction apparatus for 3 hr
filtrationThe suspension was filtered through Celite
concentrationthe filtrate was concentrated
customto give 4.3 g
customThis material, when recrystallized from cyclohexane
customgave 3.66 g

Sources & evidence

ORD record: ord-d2e62b66509d468f8d2a54fdb30e4c3d
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04585785

Reaction notes

Loading…