Triethylamine → 8-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane

HRID 1095493Notes

Reaction equation

[C:1]1([C:7]2(C(O)=O)[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:22]([CH2:25]C)CC)C.[N-]=[N+]=[N-].C1([O:36]P(=O)(O)OC2C=CC=CC=2)C=CC=CC=1>C1(OC)C=CC=CC=1>[N:22]([C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][C:10]2([O:11][CH2:12][CH2:13][O:14]2)[CH2:15][CH2:16]1)=[C:25]=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

8-Phenyl-1,4-dioxaspiro[4.5]decane-8-carboxylic acid (3 g, 11.5 mmol) was initially introduced into anisole (30 ml). The suspension obtained was cooled to a temperature of 0° C. in an ice/sodium chloride bath and triethylamine (2.25 ml, 16 mmol) was added. A clear solutions was formed and was stirred at 0° C. for a further 15 min. Phosphoric acid diphenyl ester azide (2.5 ml, 11.5 mmol) was then added to the mixture in the course of 5 min. The reaction mixture was stirred at 0° C. for 20 min, allowed to come to RT in the course of a further 20 min and then heated in an oil bath at 100° C. (bath temperature) for 2 h. For working up, the anisole was distilled off under an oil pump vacuum. Purification by chromatography was carried out on silica gel with toluene. The desired product was obtained as a crystalline solid with a melting point of 38-41° C. in a yield of 2.7 g (91%).

Workup

customThe suspension obtained
customA clear solutions was formed
stirringThe reaction mixture was stirred at 0° C. for 20 min
customto come to RT in the course of a further 20 min
temperatureheated in an oil bath at 100° C. (bath temperature) for 2 h
distillationthe anisole was distilled off under an oil pump vacuum
customPurification by chromatography

Sources & evidence

ORD record: ord-5dcfc37637ef4797ad244cfca0bbf9e4
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138187B2

Reaction notes

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