p-Toluenesulfonic acid → 1'-Benzoyl-3,4-dihydro-6-methoxy-spiro[(2H)-1-benzopyran-2,4'-piperidine]

HRID 1591225Notes

Reaction equation

HRID 1591225 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:19][C:18](=O)[C:17]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:16]=3[O:15]2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>[Pd]>[C:1]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:19][CH2:18][C:17]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:16]=3[O:15]2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 190454151'-Benzoyl-3,4-dihydro-6-methoxy-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one

Product 1

HCID 190455501'-Benzoyl-3,4-dihydro-6-methoxy-spiro[(2H)-1-benzopyran-2,4'-piperidine]Yield 54%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the procedures as described in Example 435, 1'-benzoyl-3,4-dihydro-6-methoxy-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one was reduced with sodium borohydride, dehydrated with p-toluenesulfonic acid and hydrogenated with palladium on carbon (5%) under hydrogen (50 psi) to give the piperidine as a foam (54%).

Sources & evidence

ORD record
ord-a81e813577e44e6aa76dae358fa39eef
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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