1-Tetrahydro-2H-pyran-4-ylpiperidine-4-carboxylic acid → {(3S,4R)-4-(3,4-dichloro-phenyl)-1-[1-(tetrahydro-pyran-4-yl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester

HRID 587365Notes

Reaction equation

HRID 587365 reaction equation
[F:1][C:2]([F:28])([F:27])[CH:3]1[CH2:8][CH2:7][CH:6]([O:9][C:10](=[O:26])[N:11]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[CH2:16][NH:15][CH2:14]2)[CH3:12])[CH2:5][CH2:4]1.[O:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:40][CH2:39][CH:38]([C:41](O)=[O:42])[CH2:37][CH2:36]2)[CH2:31][CH2:30]1>>[F:28][C:2]([F:1])([F:27])[CH:3]1[CH2:8][CH2:7][CH:6]([O:9][C:10](=[O:26])[N:11]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[CH2:16][N:15]([C:41]([CH:38]3[CH2:39][CH2:40][N:35]([CH:32]4[CH2:33][CH2:34][O:29][CH2:30][CH2:31]4)[CH2:36][CH2:37]3)=[O:42])[CH2:14]2)[CH3:12])[CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 252204681-Tetrahydro-2H-pyran-4-ylpiperidine-4-carboxylic acidHCID 67234197[(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester

Product 1

HCID 58303099{(3S,4R)-4-(3,4-dichloro-phenyl)-1-[1-(tetrahydro-pyran-4-yl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound {(3S,4R)-4-(3,4-dichloro-phenyl)-1-[1-(tetrahydro-pyran-4-yl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester was prepared from [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-trifluoromethyl-cyclohexyl ester instead of [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using 1-(tetrahydro-pyran-4-yl)-piperidine-4-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as an off-white foam. MS m/e: 634.2 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as an off-white foam

Sources & evidence

ORD record
ord-a178b7a27d684cf7b6b1cea34d1b8544
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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