HCID 21493357, compound → HCID 21493363, compound

HRID 1973283Notes

Reaction equation

HRID 1973283 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][C:9]2([C:19]3[C:14](=[CH:15][C:16]([O:20]C)=[CH:17][CH:18]=3)[CH:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:12]2)[CH2:8][CH2:7]1)([CH3:4])=[O:3].CP(CN1CCC2(C3C(=CC=CC=3)C(C3C=CC(OC)=CC=3)O2)CC1)(C)=O>>[CH3:4][P:2]([CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[CH:13]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:12]2)[CH2:10][CH2:11]1)([CH3:1])=[O:3]

Participants

3

Reactant 2

HCID 21493357HCID 21493357, compoundHCID 21493360HCID 21493360, compound

Product 1

HCID 21493363HCID 21493363, compound

Procedure

A solution of 1,3-dihydro-1'-dimethylphosphinylmethyl-6-methoxy-3-phenylspiro[isobenzofuran-1,4'-piperidine] and 48% hydrobromic acid is heated under reflux, cooled, diluted with water, neutralized with sodium bicarbonate and extracted with chloroform. The chloroform solution is dried and the chloroform evaporated off, affording 1,3-dihydro-1'-dimethylphosphinylmethyl-6-hydroxy-3-phenylspiro[isobenzofuran-1,4'-piperidine]. In an analogous manner, 1,3-dihydro-1'-dimethylphosphinylmethyl-5-methoxy-3-phenylspiro[isobenzofuran-1,4'-piperidine] and 1,3-dihydro-1'-dimethylphosphinylmethyl-3-(4-methoxyphenyl)spiro[isobenzofuran-1,4'-piperidine] are treated to provide 1,3-dihydro-1'-dimethylphosphinylmethyl-5-hydroxy-3-phenylspiro[isobenzofuran-1,4'-piperidine] and 1,3-dimethylphosphinylmethyl-3-(4-hydroxyphenyl)spiro[isobenzofuran-1,4'-piperidine], respectively.

Sources & evidence

ORD record
ord-5a7c3477aa4f4913ad2ccf8e0310749d
Source dataset
uspto-grants-1976_12
Patent number
US03996354

Reaction notes

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