Hydrochloric Acid → Ethyl 3-(phenylethynyl)-1-oxa-8-azaspiro[4.5]dec-3-ene-8-carboxylate

HRID 2040852Notes

Reaction equation

HRID 2040852 reaction equation
O[C:2]1([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][C:5]2([CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7]2)[O:4][CH2:3]1.S(Cl)(Cl)=O.O.Cl>N1C=CC=CC=1>[C:19]1([C:18]#[C:17][C:2]2[CH2:3][O:4][C:5]3([CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7]3)[CH:6]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24386Thionyl ChlorideHCID 57493817Ethyl 3-hydroxy-3-(2-phenylethynyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 57493818Ethyl 3-(phenylethynyl)-1-oxa-8-azaspiro[4.5]dec-3-ene-8-carboxylateYield 20.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Compound 26a (93 mg, 0.282 mmol) stirred in pyridine (4 mL) at 0° C. was added thionyl chloride (0.103 mL, 1.141 mmol) and the reaction mixture was stirred at 0° C. to r.t. for 2 h. Afterwards, it was poured into water, acidified with 1M HCl and extracted with chloroform. The organic layers were combined, washed with brine, dried over sodium sulphate and evaporated to dryness to afford a crude, which was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 92:8 to 75:25) to give 18 mg of the title compound.

Workup

  1. extractionextracted with chloroform
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness
  5. customto afford a crude, which
  6. customwas purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 92:8 to 75:25)

Sources & evidence

ORD record
ord-d27d0a8fcb3c4e8da2b770f728777666
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

Loading…