Trifluoroacetic acid → HCID 68592998, compound

HRID 2220996Notes

Reaction equation

HRID 2220996 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>[F:19][C:18]([F:21])([F:20])[C:16]([OH:22])=[O:17].[OH:15][CH2:14][C@@H:4]1[NH:5][CH2:6][C@H:2]([OH:1])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10680283tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 68592998HCID 68592998, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl(2R,4R)-4-hydroxy-2-(hydroxymethyl)-1-pyrrolidinecarboxylate (0.185 g, 0.852 mmol) was stirred in a 1:1 solution of methylene chloride:TFA for 14 hours. The reaction was concentrated, and the crude material was used without further purification. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.5 (m, 1 H), 2.2 (m, 4 H), 3.0 (m, 1 H), 3.1 (m, 1 H), 3.6 (m, 3 H), 4.3 (m, 1 H), 5.3 (s,br, 2 H), 8.6 (s,br, 1 H), 9.2 (s,br, 1 H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude material was used without further purification

Sources & evidence

ORD record
ord-2930893eaf8b4f4e9681ce185f02b3d6
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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