Trifluoroacetic acid → Trifluoroacetic acid

HRID 1852736Notes

Reaction equation

HRID 1852736 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-84a8c3d835a04114bf0fc2f8fbe7c18f
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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