Triethylamine → 3.4,5.6-Tetrahydrophthalimidomethyl dispiro(2.0.4.1)nonane-9-Carboxylate

HRID 1111683

Reaction equation

HRID 1111683 reaction equation
[CH2:1]1[C:3]2([CH:9]([C:10]([OH:12])=[O:11])[C:4]32[CH2:8][CH2:7][CH2:6][CH2:5]3)[CH2:2]1.S(Cl)(Cl)=O.O[CH2:18][N:19]1[C:23](=[O:24])[C:22]2[CH2:25][CH2:26][CH2:27][CH2:28][C:21]=2[C:20]1=[O:29].C(N(CC)CC)C>C1C=CC=CC=1.CCOCC>[CH2:2]1[C:3]2([CH:9]([C:10]([O:12][CH2:18][N:19]3[C:20](=[O:29])[C:21]4[CH2:28][CH2:27][CH2:26][CH2:25][C:22]=4[C:23]3=[O:24])=[O:11])[C:4]32[CH2:5][CH2:6][CH2:7][CH2:8]3)[CH2:1]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 78597N-(Hydroxymethyl)-3,4,5,6-tetrahydrophthalimideHCID 22767648Dispiro(2.0.4.1)nonan-9-carboxylic acid

Product 1

HCID 227676553.4,5.6-Tetrahydrophthalimidomethyl dispiro(2.0.4.1)nonane-9-Carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

Dispiro(2.0.4.1)nonan-9-carboxylic acid (0.66g) was converted to the corresponding acid chloride by refluxing with thionyl chloride (1ml) in benzene (20 ml) for 1 hour. The acid chloride, N-hydroxymethyl-3,4,5,6-tetrahydrophthalimide (0.7g) and triethylamine (0.5g) were then stirred together in ether (50 ml) for 6 hours. After removal of solvent under reduced pressure the residue was purified by chromatography on silica gel using dichloromethane as eluent. The required product was obtained as an oil R.I. nD18 1.5318.

Workup

  1. customAfter removal of solvent under reduced pressure the residue
  2. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-aaf3ae2a005040e89a8cd44fc2b3e927
Source dataset
uspto-grants-1978_10
Patent number
US04118510

Linked notes

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