Trifluoroacetic acid → Trifluoroacetic acid

HRID 81133Notes

Reaction equation

HRID 81133 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([CH2:14][OH:15])[CH2:3]1.[C:16]([OH:22])([C:18]([F:21])([F:20])[F:19])=[O:17]>C(Cl)Cl>[OH:15][CH2:14][C@H:4]1[NH:5][CH2:6][C@H:2]([OH:1])[CH2:3]1.[C:16]([OH:22])([C:18]([F:21])([F:20])[F:19])=[O:17]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11275979N-Boc-trans-4-hydroxy-L-prolinol

Product 2

HCID 6422Trifluoroacetic acidHCID 15817396(3R,5S)-5-(Hydroxymethyl)pyrrolidin-3-OL

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (498.5 mg, 2.29 mmol) dissolved in DCM (6.8 mL) was added TFA (0.85 mL). The mixture was stirred for 16 hours. The mixture was concentrated to give (3R,5S)-5-(hydroxymethyl)pyrrolidin-3-ol as a TFA salt.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-3f5d8d5502b94c38ac7d5a18bbf70ff7
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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