HCID 69585940, compound → HCID 11324971, compound

HRID 1242074Notes

Reaction equation

HRID 1242074 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:15][CH2:14][C:9]2(OCC[O:10]2)[CH2:8][CH:7]1[CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27])=[O:5])[CH3:2]>Cl.O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:15][CH2:14][C:9](=[O:10])[CH2:8][CH:7]1[CH2:16][N:17]1[C:18](=[O:27])[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]1=[O:26])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 69585940HCID 69585940, compound

Product 1

HCID 11324971HCID 11324971, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A solution of the above 7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid ethyl ester (0.44 g, 1.2 mmol) in a mixture of 1N hydrochloric acid (18 ml) and tetrahydrofuran (18 ml) was heated a 75° C. under nitrogen with stirring for 18 h. The tetrahydrofuran was removed in vacuo and the residue was extracted with dichloromethane (2×75 ml). The combined organic extracts were washed with a saturated sodium bicarbonate solution (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo affording 0.42 g (>100%) of 2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-oxo-piperidine-1-carboxylic acid ethyl ester as a solid.

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. extractionthe residue was extracted with dichloromethane (2×75 ml)
  3. washThe combined organic extracts were washed with a saturated sodium bicarbonate solution (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f3e20ce0172b45db87030754689b9751
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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