Trifluoroacetic acid → Trifluoroacetic acid

HRID 81129Notes

Reaction equation

HRID 81129 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([CH:14]([CH3:16])[CH3:15])[CH2:3]1.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[CH3:15][CH:14]([C@H:4]1[NH:5][CH2:6][C@H:2]([OH:1])[CH2:3]1)[CH3:16].[C:19]([OH:21])([C:18]([F:23])([F:22])[F:17])=[O:20]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60054987tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 60054971(3R,5S)-5-(propan-2-yl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate (500 mg, 2.180 mmol) dissolved in dichloromethane (5.4 mL) was added trifluoroacetic acid (1.8 mL). The reaction was stirred for 16 hours at room temperature. The mixture was concentrated to afford (3R,5S)-5-(propan-2-yl)pyrrolidin-3-ol as a TFA salt. 1H NMR (500 MHz, CDCl3) δ 3.91-3.62 (m, 1H), 3.60-3.36 (m, 2H), 2.47-2.10 (m, 2H), 2.05-1.79 (m, 2H), 1.07 (d, J=6.6, 3H), 1.01 (d, J=6.7, 3H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-52f8d82c94c5449c864c4573ace5c929
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…