Water → HCID 21488274, compound

HRID 1974011Notes

Reaction equation

HRID 1974011 reaction equation
O[CH:2]1[CH2:9][CH2:8][CH:7]([OH:10])[CH:6]2[N:11]([CH3:12])[CH:3]1[CH2:4][CH2:5]2.[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][C:29]([OH:31])=[O:30])[CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])([CH3:16])([CH3:15])[CH3:14].[OH2:32]>C1(C)C(C)=CC=CC=1.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][C:29]([O:31][CH:3]2[CH2:4][CH2:5][CH:6]3[N:11]([CH3:12])[CH:2]2[CH2:9][CH2:8][CH:7]3[O:10][C:29](=[O:30])[CH2:28][C:19]2[CH:20]=[C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])[C:22]([OH:32])=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:18]=2)=[O:30])[CH:20]=[C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])[C:22]=1[OH:23])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 27751103,5-Bis(1,1-dimethylethyl)-4-hydroxybenzeneacetic acidHCID 214882869-Methyl-9-azabicyclo[4.2.1]nonane-2,5-diol

Product 1

HCID 21488274HCID 21488274, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 7237O-XyleneSolvent

Procedure

Under nitrogen a stirred solution of the diol mixture 2,6-dihydroxy-9-methyl-9-azabicyclo [3.3.1]nonane and 2,5-dihydroxy-9-methyl-9-azabicyclo[4.2.1]nonane (4.28 g, 0.025 mole), 3,5-di-tert-butyl-4-hydroxyphenylacetic acid (14.55 g, 0.055 mole) and titanium tetraisopropylate (0.7 ml) in 100 ml of xylene was heated under reflux for 18 hours water being removed with a Dean-Stark trap. The xylene was evaporated under reduced pressure and the residue was dissolved in ether. The ether solution was washed with water then 10% aqueous sodium hydroxide and again with water. The dried (Na2SO4) solution was crystallized from petroleum ether and then from hexane to give 4.6 g (28%) of the desired ester, m.p. 98°-100° C.

Workup

  1. customremoved with a Dean-Stark trap
  2. customThe xylene was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washThe ether solution was washed with water
  5. dry with materialThe dried (Na2SO4) solution
  6. customwas crystallized from petroleum ether

Sources & evidence

ORD record
ord-19cc62e005ae4e4f90cdeef9a1da2de5
Source dataset
uspto-grants-1976_12
Patent number
US04000113

Reaction notes

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