Ammonium Chloride → (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol

HRID 1599134Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH:12]([CH2:18][O:19][S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:13][C:14]2=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:14]1([OH:17])[CH2:13][CH:12]([CH2:18][O:19][S:20]([C:23]2[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=2)(=[O:22])=[O:21])[CH2:11][CH:10]2[CH:15]1[CH2:16][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 12.07 g .of (3aRS,6SR,7aSR)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-one in 50 cm3 of anhydrous tetrahydrofuran is run over a period of 15 minutes into a suspension, cooled to +5° C., of 2-methoxyphenylmagnesiumbromide (prepared from 6.4 cm3 of 2-bromoanisole and 1.24 g of magnesium) in 200 cm3 of anhydrous tetrahydrofuran. The reaction mixture is stirred at 20° C. for one hour, cooled to +5° C., treated with 250 cm3 of saturated aqueous ammonium chloride solution and extracted with 200 cm3 of ethyl acetate. The organic phase is washed with 300 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The oily residue is recrystallized from a mixture of ethyl acetate and diisopropyl ether, and the crystals are filtered, washed with diisopropyl ether, subjected to suction and then dried under reduced pressure (2.7 kPa). 11.38 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol are obtained in the form of white crystals. M.p.K =153° C.

Workup

temperaturecooled to +5° C.
extractionextracted with 200 cm3 of ethyl acetate
washThe organic phase is washed with 300 cm3 of water
dry with materialdried over magnesium sulphate
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe oily residue is recrystallized from a mixture of ethyl acetate and diisopropyl ether
filtrationthe crystals are filtered
washwashed with diisopropyl ether
customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-51ca2467a27c4cdab7d24aece2525723
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

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