Thionyl Chloride → (3aR,7S,7aR)-2-tert-butyloxycarbonyl-7-chloro-4,4-diphenylperhydroisoindole

HRID 1721199Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:16][C@H:15]2[C@H:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:13][C@@H:14]2O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:32])=O>>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]2[C@@H:15]([C@@H:14]([Cl:32])[CH2:13][CH2:12][C:11]2([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 11003741(3aR,4S,7aR)-2-t-butoxycarbonyl-7,7-diphenyl-4-perhydroisoindolol

Product 1

HCID 57032796(3aR,7S,7aR)-2-tert-butyloxycarbonyl-7-chloro-4,4-diphenylperhydroisoindole

Procedure

A solution of 1 g of (3aR, 4S, 7aR)-2-tert-butyloxycarbonyl-7,7-diphenyl-4-perhydroisoindolol in 10 cm3 of thionyl chloride is stirred for 3 hours at 80° C. The reaction mixture is then concentrated to dryness under reduced pressure (2.7 kPa). 1.03 g of (3aR, 7S, 7aR)-2-tert-butyloxycarbonyl-7-chloro-4,4-diphenylperhydroisoindole are obtained in the form of a solid which is used in the crude state in the following test.

Workup

concentrationThe reaction mixture is then concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-9dc958acaabc4e3f8686f896f1ee47c5
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05508433

Reaction notes

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