Trifluoroacetic acid → Trifluoroacetic acid

HRID 81132Notes

Reaction equation

HRID 81132 reaction equation
[OH:1][C:2]1([CH3:17])[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([CH:14]([CH3:16])[CH3:15])[CH2:3]1.[C:18]([OH:24])([C:20]([F:23])([F:22])[F:21])=[O:19]>C(Cl)Cl>[CH3:17][C:2]1([OH:1])[CH2:3][C@@H:4]([CH:14]([CH3:16])[CH3:15])[NH:5][CH2:6]1.[C:18]([OH:24])([C:20]([F:23])([F:22])[F:21])=[O:19]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724491tert-butyl (2S)-4-hydroxy-4-methyl-2-(propan-2-yl)pyrrolidine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 86724492(5S)-3-methyl-5-(propan-2-yl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (2S)-4-hydroxy-4-methyl-2-(propan-2-yl)pyrrolidine-1-carboxylate (532.2 mg, 2.18 mmol) dissolved in DCM (5.5 mL) was added TFA (1.8 mL). The mixture was stirred for 16 hours. The mixture was concentrated to give (5S)-3-methyl-5-(propan-2-yl)pyrrolidin-3-ol as a TFA salt. 1H NMR (500 MHz, CDCl3) δ 3.76 (s, 1H), 3.49-3.34 (m, 2H), 2.29-2.17 (m, 1H), 2.06-1.95 (m, 2H), 1.51 (s, 3H), 1.07-0.97 (m, 7H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4cd05d2cd3a04a37b9df8517dc695b18
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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