tert-Butyl piperazine-1-carboxylate → (2S,5R)-4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-nitrophenyl]-2,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester

HRID 1038609Notes

Reaction equation

HRID 1038609 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[F:16][C:17]([F:35])([F:34])[C:18]([C:24]1[CH:29]=[CH:28][C:27](F)=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)([OH:23])[C:19]([F:22])([F:21])[F:20].N1(C(OC(C)(C)C)=O)CCNCC1>>[C:12]([O:11][C:9]([N:3]1[CH2:4][C@@H:5]([CH3:8])[N:6]([C:27]2[CH:28]=[CH:29][C:24]([C:18]([OH:23])([C:17]([F:35])([F:34])[F:16])[C:19]([F:20])([F:21])[F:22])=[CH:25][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:7][C@@H:2]1[CH3:1])=[O:10])([CH3:13])([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 11745988(2S,5R)-1-Boc-2,5-dimethylpiperazineHCID 866472101,1,1,3,3,3-Hexafluoro-2-(4-fluoro-3-nitrophenyl)propan-2-ol

Product 1

HCID 86647215(2S,5R)-4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-nitrophenyl]-2,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester

Procedure

Similar reaction and treatment as Example 43-b) was conducted except that (2S,5R)-tert-butyl 2,5-dimethylpiperazine-1-carboxylate obtained in Example 14-1-a-2-2) was used in place of 1,1,1,3,3,3-hexafluoro-2-(4-fluoro-3-nitrophenyl)propan-2-ol obtained in Example 43-a) and tert-butyl piperazine-1-carboxylate, and the title compound was obtained as a yellow oil.

Workup

  1. customSimilar reaction and treatment as Example 43-b)

Sources & evidence

ORD record
ord-eddf081d90894772b7267bffec169926
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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