Pseudoephedrine → Pseudoephedrine

HRID 1613503Notes

Reaction equation

[C:1]([O:5][C:6]([CH:8]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:9][C:10]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C@H:25]([NH:34][CH3:35])[C@@H:26]([OH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCCCCC>[CH3:24][C@H:25]([NH:34][CH3:35])[C@@H:26]([OH:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1.[C:1]([O:5][C:6]([C@H:8]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:9][C:10]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid (110.1 g, 0.333 mole) in hexane (550 ml) was treated with (+) pseudoephedrine (55.1 g, 0.333 mole) and the mixture was heated to reflux. The resulting solution was cooled to induce crystallisation, and stirred at 5° C. for 1 hour to granulate the crystals. After overnight refrigeration at 5° C., filtration, washing with hexane (200 ml) and drying gave the crude (+) pseudoephedrine salt of the (S) acid (89.9 g, 54.4%) as a white solid m.p. 76°-80° C. Recrystallisation of 30 g of this material twice from hexane (225 ml) gave the (+) pseudoephedrine salt of the title compound (21.45 g, 71.5% recovery) as white crystals m.p. 86°-7° C., [α]D +34.9° (c=1, MeOH). Found: C,65.21; H,9.23; N,2.91. C27H45NO7 requires C,65.42; H,9.15; N,2.82%.

Workup

temperaturethe mixture was heated to reflux
temperatureThe resulting solution was cooled
customcrystallisation
waitAfter overnight refrigeration at 5° C.
filtrationfiltration
washwashing with hexane (200 ml)
customdrying

Sources & evidence

ORD record: ord-0763667d7bf84f84b964b19dd686c7d7
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05192800

Reaction notes

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