Toluene → HCID 20286520, compound

HRID 127257Notes

Reaction equation

HRID 127257 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][C:14]([C:18]([CH3:23])([CH3:22])C(O)=O)([OH:17])[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.C1(C)C=CC=CC=1>ClCCl>[CH3:23][C:18]1([CH3:22])[C:14]2([CH2:13][CH2:12][N:11]([C:1]([O:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:2])[CH2:16][CH2:15]2)[O:17][C:46](=[O:31])[NH:43]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 20286545HCID 20286545, compound

Product 1

HCID 20286520HCID 20286520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(1-carbobenzyloxy-4-hydroxypiperidin-4-yl)-2-methylpropionic acid, 1.29 g diphenylphosphoryl azide, 0.47 g triethylamine and 50 ml toluene is heated at reflux for 18 hours. Evaporation of solvent gives a residue which is taken up in 125 ml dichloromethane and is washed with 50 ml 1 N hydrochloric acid and 50 ml, 5% sodium bicarbonate. Evaporation of the solvent followed by trituration with diethyl ether affords 1.86 g 4,4-dimethyl-8-carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 208°-209°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. customEvaporation of solvent
  4. customgives a residue which
  5. washis washed with 50 ml 1 N hydrochloric acid and 50 ml, 5% sodium bicarbonate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fd64a91e3aa449b68056df1ef3303d11
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Reaction notes

Loading…