Hydrochloric Acid → HCID 22857049, compound

HRID 2211410Notes

Reaction equation

HRID 2211410 reaction equation
[C:1]1([C:7]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:15]3[C@@H:11]([CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14]3)[C@@:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])(O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:38]>C(O)(=O)C>[ClH:38].[C:32]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH:9]=[C:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[C@H:11]3[C@@H:15]2[CH2:14][NH:13][CH2:12]3)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22857048HCID 22857048, compound

Product 1

HCID 22857049HCID 22857049, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8.56 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-tert-butoxycarbonyl-perhydroisoindol-4-ol in 53 cm3 of acetic acid and 30 cm3 of 12N hydrochloric acid is heated at 95° C. for 45 minutes, and then cooled to room temperature and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallised from 20 cm3 of acetonitrile. 5.2 g of (3aS,7aR)-4,4-diphenyl-7-(2-methoxyphenyl)-2,3,3a, 4,5,7a-hexahydroisoindole hydrochloride are obtained in the form of white crystals which melt at a temperature above 300° C., and the product is used in the crude state in the subsequent syntheses.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  2. customThe residue is recrystallised from 20 cm3 of acetonitrile

Sources & evidence

ORD record
ord-2f900bf2c8484294ac0ea55502ed1e00
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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