Hydrochloric Acid → (3aR, 7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride

HRID 2399992Notes

Reaction equation

C(OC([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([C@H:11]([F:29])[CH2:12][CH2:13][C:14]2([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)=O)(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[C:23]1([C:14]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12][C@@H:11]([F:29])[C@@H:10]3[C@H:15]2[CH2:16][NH:8][CH2:9]3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 2.25 g of (3aR,7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole in 25 cm3 of dioxane is treated with a 5.8N solution of hydrochloric acid in dioxane and stirred for 2 hours at 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is concentrated by adding 100 cm3 of isopropyl oxide, the solid is filtered and dried to give 1.8 g of (3aR,7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride, in the form of a cream-colored powder. Proton NMR spectrum (DMSO-d6): 1.0-1.35 (mt, 1H of CH2 in 6); 4.9 (broad d, J=50, 1H, CHF); 7.1 to 7.5 (mt, 14H, aromatics); 9.05 and 9.9 (2 mf, 2×1H, NH2+).

Workup

concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
concentrationThe residue is concentrated
additionby adding 100 cm3 of isopropyl oxide
filtrationthe solid is filtered
customdried

Sources & evidence

ORD record: ord-9ca560f141ff48769de5734b5bf4892d
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05451601

Reaction notes

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