1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)piperidine-4-carboxylic acid → {(3S,4R)-4-(4-chloro-phenyl)-1-[1-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-fluoro-phenyl ester

HRID 587356Notes

Reaction equation

HRID 587356 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[O:25]=[S:26]1(=[O:41])[CH2:31][CH2:30][CH:29]([N:32]2[CH2:37][CH2:36][CH:35]([C:38](O)=[O:39])[CH2:34][CH2:33]2)[CH2:28][CH2:27]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:38]([CH:35]3[CH2:34][CH2:33][N:32]([CH:29]4[CH2:30][CH2:31][S:26](=[O:41])(=[O:25])[CH2:27][CH2:28]4)[CH2:37][CH2:36]3)=[O:39])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 650562141-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)piperidine-4-carboxylic acidHCID 67233751[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Product 1

HCID 58303091{(3S,4R)-4-(4-chloro-phenyl)-1-[1-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-fluoro-phenyl ester

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound {(3S,4R)-4-(4-chloro-phenyl)-1-[1-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from [(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using 1-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-piperidine-4-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as an off-white foam. MS m/e: 592.2 [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-3f8c5f81b66f4a108aadc168768a9f62
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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