Trityl chloride → 1-((3R,4R)-3-hydroxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

HRID 1666676Notes

Reaction equation

HRID 1666676 reaction equation
[NH2:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8](=[O:21])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH2:3]1.C(N(CC)CC)C.[C:29]1([C:35](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl.C1COCC1>[OH:7][C@H:6]1[C@H:2]([NH:1][C:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:3][N:4]([C:8](=[O:21])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[CH2:5]1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 579701111-((3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

Product 1

HCID 674451821-((3R,4R)-3-hydroxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanoneYield 61.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-((3R,4R)-3-Amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (1.0 g) was dissolved in chloroform (30 mL) and THF (10 mL), followed by addition of triethylamine (0.55 mL) and triphenylmethyl chloride (1.4 g), and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=4:1-2:1) to obtain 1-((3R,4R)-3-hydroxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (1.1 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-f109ecd7c54347d1b0191eab99696a0c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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