Diketene → 1-Benzylpiperidin-3-yl 3-oxobutanoate

HRID 544255Notes

Reaction equation

HRID 544255 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]=[C:16]1[O:20][C:18](=[O:19])[CH2:17]1>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:18](=[O:19])[CH2:17][C:16]([CH3:15])=[O:20])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 12661DiketeneHCID 857731-Benzylpiperidin-3-ol

Product 1

HCID 135193571-Benzylpiperidin-3-yl 3-oxobutanoateYield 62.7%

Procedure

Then, 11.8 g of the 1-benzyl-3-hydroxypiperidine and 5.6 g of diketene were reacted similarly as in Reference Example 1, and the reaction product was purified by silica gel column chromatography (eluent:chloroform:methanol=9:1 v/v), to obtain 10.65 g of acetoacetic acid-N-benzyl-3-piperidinyl ester (yield: 62.5%). This was used in the reaction of Example 4 without distillation.

Workup

  1. customthe reaction product was purified by silica gel column chromatography (eluent:chloroform:methanol=9:1 v/v)

Sources & evidence

ORD record
ord-6995a1bc01b3463fa28fbe308a99dda6
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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