3-Piperidinecarboxamide → tert-Butyl (3R)-3-carbamoylpiperidine-1-carboxylate

HRID 2195604Notes

Reaction equation

[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([NH2:6])=[O:5])[CH2:2]1.[C:10](OC([O-])=O)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>>[C:13]([O:12][C:10]([N:1]1[CH2:9][CH2:8][CH2:7][C@@H:3]([C:4]([NH2:6])=[O:5])[CH2:2]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 929803-Piperidinecarboxamide

HCID 22064466Tert-butyldicarbonate

Product 1

HCID 26343680tert-Butyl (3R)-3-carbamoylpiperidine-1-carboxylateYield 39%

Procedure

To the reaction mixture obtained in Example 4, tert-butyl dicarbonate (16.1 g, 1.0 equivalent) was added. The pH of the reaction mixture was kept from 7.0 to 8.0. The reaction mixture was stirred for 3 hours at room temperature to obtain a solution containing (R)-1-(tert-butoxycarbonyl)nipecotamide (6.6 g, yield: 39%).

Workup

customto obtain a solution

Sources & evidence

ORD record: ord-46a6892738654177be5e8e5b2eed7f43
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338142B2

Reaction notes

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