(2R,4S)-4-{(3,5-Bis-trifluoromethyl-benzyl)-[5-((E)-2-methoxycarbonyl-vinyl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester → (2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methoxycarbonyl-ethyl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 409459Notes

Reaction equation

HRID 409459 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[C:14]2[N:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH2:41][CH3:42])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:38])[F:39])[CH:28]=2)[C:14]2[N:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][N:19]=2)[CH2:10][C@H:9]1[CH2:41][CH3:42])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86648398(2R,4S)-4-{(3,5-Bis-trifluoromethyl-benzyl)-[5-((E)-2-methoxycarbonyl-vinyl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86648397(2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methoxycarbonyl-ethyl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2R,4S)-4-{(3,5-Bis-trifluoromethyl-benzyl)-[5-((E)-2-methoxycarbonyl-vinyl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (200 mg, 0.33 mmol) is dissolved in EtOH (5 mL) and hydrogenation reaction with 10% Pd/C. The residue is purified by column chromatography on silica gel (eluent: n-hexane/EtOAc) to give (2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methoxycarbonyl-ethyl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (198 mg, 99%).

Workup

  1. customThe residue is purified by column chromatography on silica gel (eluent: n-hexane/EtOAc)

Sources & evidence

ORD record
ord-cac4cd76e515411a90acbd2711b70af6
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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