Acetaldehyde → 4-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 2386463Notes

Reaction equation

HRID 2386463 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[CH:5]=[CH:4][N:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH:30](=O)[CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:9]=2)[CH2:30][CH3:31])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehyde

Product 1

HCID 866032904-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Procedure

Intermediate 1 was coupled with 4-Amino-piperidine-1-carboxylic acid tert-butyl ester following procedure B. When the starting aldehyde had been consumed, 2 equivalents each of acetaldehyde and sodium triacetoxyborohydride were added and the mixture stirred for another two hours. The organic layer was washed with, water followed by sat. NaCl. The solvent was removed to give product LC-MS showed the product was >90% pure and had the expected M+H+ of 403, and it was used in the following reactions without purification.

Workup

  1. customWhen the starting aldehyde had been consumed
  2. washThe organic layer was washed with, water
  3. customThe solvent was removed
  4. customto give product LC-MS
  5. customwas used in the following reactions without purification

Sources & evidence

ORD record
ord-bc3a9441f9d64ffbb83faef813b0ce04
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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