HCID 18687527, compound → HCID 3698157, compound

HRID 1872759Notes

Reaction equation

HRID 1872759 reaction equation
O[CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:3]1[N:12]([C:13]([O:15]C(C)(C)C)=[O:14])[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4]1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[C:20]1([CH:2]2[CH:3]3[CH2:4][C:5]4([O:9][CH2:8][CH2:7][O:6]4)[CH2:10][CH2:11][N:12]3[C:13](=[O:15])[O:14]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 18687527HCID 18687527, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 3698157HCID 3698157, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (±)-1,1-dimethylethyl 7-(hydroxyphenylmethyl)-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate (183.6 g) and potassium tert-butoxide (6 g) in toluene (900 ml) was stirred and refluxed for 2 hours. The solvent was evaporated and the residue was stirred in petrol ether and water. The mixture was decanted and the residue was stirred up in DIPE. The precipitate was filtered off and dried, yielding 127.4 g (92%) of (±)-tetrahydro-1'-phenylspiro(1,3-dioxolan-2,7'(8'H)-3H-oxazolo[3,4-a]pyridin)-3'-one (interm. 2).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvent was evaporated
  3. stirringthe residue was stirred in petrol ether
  4. customThe mixture was decanted
  5. stirringthe residue was stirred up in DIPE
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-e1d79e43b80e4be4953dd8bf2c7bf0c8
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

Loading…