Isocaproaldehyde → Methyl{(2s,4r)-1-[(1r)-1-(1h-1,2,3-benzotriazol-1-yl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

HRID 1942306Notes

Reaction equation

HRID 1942306 reaction equation
C[CH:2]([C@@H:6]1[CH2:11][CH2:10][NH:9][C@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH2:7]1)[C:3]([O-:5])=[O:4].[CH3:22][CH:23]([CH3:28])[CH2:24][CH2:25][CH:26]=O.[NH:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[N:30]1.[C:38]1(C)C=CC=CC=1>>[CH3:38][O:5][C:3](=[O:4])[CH2:2][C@@H:6]1[CH2:11][CH2:10][N:9]([C@H:26]([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[N:30]2)[CH2:25][CH2:24][CH:23]([CH3:28])[CH3:22])[C@H:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:16][CH:17]=2)[CH2:7]1

Participants

5

Reactant 4

HCID 129IsocaproaldehydeHCID 1140TolueneHCID 86617999(+)-methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate2×HCID 178418385HCID 178418385, compound

Product 1

HCID 131730270Methyl{(2s,4r)-1-[(1r)-1-(1h-1,2,3-benzotriazol-1-yl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

Conditions

Temperature
150 °C

Procedure

A mixture of (±)-methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Intermediate 1, 453 mg, 1.5 mmol), 4-methylpentanal (150 mg, 1.5 mmol) and benzotriazole (178.5 mg, 1.5 mmol) were combined in toluene (15 ml) and the reaction was stirred and heated a 150° C. under Dean-Stark conditions for 16 Hrs. The mixture was evaporated in vacuo to provide a pale gum.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto provide a pale gum

Sources & evidence

ORD record
ord-912411b3541d42e79b0f3755d69f6512
Source dataset
uspto-grants-2013_03
Patent number
US08389547B2

Reaction notes

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