Trifluoroacetic acid → (2S,3R)-2-methyl-3-vinylpyrrolidin-3-ol

HRID 907012Notes

Reaction equation

[OH:1][C@@:2]1([CH:15]=[CH2:16])[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[C@H:3]1[CH3:14].FC(F)(F)C(O)=O>>[CH3:14][C@H:3]1[C@@:2]([CH:15]=[CH2:16])([OH:1])[CH2:6][CH2:5][NH:4]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59273002tert-butyl (2S,3R)-3-hydroxy-2-methyl-3-vinylpyrrolidine-1-carboxylate

Product 1

HCID 67389951(2S,3R)-2-methyl-3-vinylpyrrolidin-3-olYield 306.2%

Procedure

To tert-butyl (2S,3R)-3-hydroxy-2-methyl-3-vinylpyrrolidine-1-carboxylate (684 mg, 2.85 mmol) was added trifluoroacetic acid (3.0 ml). The mixture was stirred at room temperature for 15 min, and concentrated under reduced pressure to give (2S,3R)-2-methyl-3-vinylpyrrolidin-3-ol (yield: 1.11 g).

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-aa41fda9d38d476cb44fa4e50a020064
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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