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

HRID 1262593Notes

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-e1620d441ad141e7b80d6dd5a6777455
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04452809

Reaction notes

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