Hydrochloric Acid → Octahydro-1h-isoindol-4-ol

HRID 1599147Notes

Reaction equation

HRID 1599147 reaction equation
Cl.OC[CH:4]1[CH2:12][CH:11]2[CH:7]([CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10]2)[C:6](C2C=CC=CC=2F)([OH:20])[CH2:5]1>O1CCOCC1>[CH2:10]1[CH:11]2[CH:7]([CH:6]([OH:20])[CH2:5][CH2:4][CH2:12]2)[CH2:8][NH:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67661831(3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-tert-butyloxycarbonylperhydroisoindol 4-ol

Product 1

HCID 18931574Octahydro-1h-isoindol-4-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

17 cm3 of a 7N solution of hydrogen chloride in dioxane is added at room temperature to a solution of 3.35 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-tert-butyloxycarbonylperhydroisoindol-4-ol in 35 cm3 of dioxane. The reaction mixture is stirred at this temperature for 2 hours, then concentrated to dryness under reduced pressure (2.7 kPa). Trituration in diisopropyl ether gives 2.77 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(]2-fluorophenyl)perhydroisoindol-4-ol in the form of a thick white foam.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-6191f2f07b2f4c46874329a78dbec2be
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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