Pivalaldehyde → HCID 67025694, compound

HRID 1951111Notes

Reaction equation

HRID 1951111 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])[CH2:10][CH:9]2[N:21]([CH3:36])[C:22](=[O:35])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=2)=[CH:4][CH:3]=1.[CH3:37][C:38]([CH3:42])([CH3:41])[CH:39]=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:37][C:38]([CH3:42])([CH3:41])[CH3:39])[CH2:17][CH2:16]3)=[O:14])[CH2:10][CH:9]2[N:21]([CH3:36])[C:22](=[O:35])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:31]([F:33])([F:32])[F:34])[CH:24]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 12417PivalaldehydeHCID 67025677HCID 67025677, compound

Product 1

HCID 67025694HCID 67025694, compound

Procedure

In analogy to the procedure described for the synthesis of example 104, the title compound N-{(3RS,4SR)-4-(4-chloro-phenyl)-1-[1-(2,2-dimethyl-propyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-4-methoxy-N-methyl-3-trifluoromethyl-benzamide was prepared from N-[(3RS,4SR)-4-(4-chloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide using trimethylacetaldehyde (75% in tert butanol) instead of acetone and was obtained as a light brown oil. MS m/e: 594.3 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 104
  2. customwas obtained as a light brown oil

Sources & evidence

ORD record
ord-109b0d90afb542b3a4f84c958a135242
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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