Trifluoroacetic acid → HCID 68592998, compound

HRID 1864490Notes

Reaction equation

HRID 1864490 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, 1H), 2.2 (m, 4H), 3.0 (m, 1H), 3.1 (m, 1H), 3.6 (m, 3H), 4.3 (m, 1H), 5.3 (s, br, 2H), 8.6 (s, br, 1H), 9.2 (s, br, 1H).

Workup

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

Sources & evidence

ORD record
ord-c024fe85139b458b96c0a4a5bd415756
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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