tert-butyl N-[(3S)-piperidin-3-yl]carbamate → tert-butyl N-methyl-N-[(3S)-piperidin-3-yl]carbamate

HRID 1409793Notes

Reaction equation

HRID 1409793 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15]NC([C@@H]1CCCNC1)=O>>[CH3:15][N:8]([C@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 7175805(3R)-N-methylpiperidine-3-carboxamide

Product 1

HCID 28875358tert-butyl N-methyl-N-[(3S)-piperidin-3-yl]carbamate

Procedure

Prepared from (S)-3-(tert-butoxycarbonylamino)piperidine in the same scale and manner as the (3R) isomer described in Preparative Example 35. Yields were 96% and 93% for the first two steps. Product yield was treated as quantitative for last step and used as reagent in a further reaction (Example 94). LC/MS 1.30 min, [M+1]+ 215.

Workup

  1. customYields
  2. customProduct yield
  3. additionwas treated as quantitative for last step
  4. customused as reagent in a further reaction (Example 94)
  5. customLC/MS 1.30 min, [M+1]+ 215

Sources & evidence

ORD record
ord-e9a45ab19a404bcc8f2bef38cb3c9aa9
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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