Water → HCID 58123694, compound

HRID 536645Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:13]2([CH3:19])[C:16]([CH3:18])([CH3:17])[CH:9]1[CH2:10][C:11]1[CH:23]=[C:22]([OH:24])[C:21]([OH:25])=[CH:20][C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([O-])([O-])=O.[K+].[K+].ICI.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:13]2([CH3:19])[C:16]([CH3:17])([CH3:18])[CH:9]1[CH2:10][C:11]1[CH:23]=[C:22]3[O:24][CH2:26][O:25][C:21]3=[CH:20][C:12]=12)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8,9-dihydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]-azocine-3-carboxylic acid tert-butyl ester (0.21 g), K2CO3 (0.19 g) and diiodomethane (54 μL) in dimethylformamide (5 mL) is heated to 100° C. and stirred at this temperature for 2 h. Then, another portion of diiodomethane (54 μL) and K2CO3 (0.18 g) is added and the mixture is further stirred at 100° C. for 5 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with brine and dried (MgSO4). After removal of the solvent, the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1).

Workup

stirringthe mixture is further stirred at 100° C. for 5 h
temperatureAfter cooling to room temperature
extractionthe resulting mixture is extracted with ethyl acetate
washThe combined organic extracts are washed with brine
dry with materialdried (MgSO4)
customAfter removal of the solvent
customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-543cf492f91e407d850516c045f985d3
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859580B2

Reaction notes

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