Hydrochloric Acid → HCID 86706742, compound

HRID 710030Notes

Reaction equation

HRID 710030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:16][OH:17].Cl>N1C=CC=CC=1>[OH:17][N:16]=[CH:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 86706742HCID 86706742, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (S)-t-butyl-2-formylpyrrolidine-1-carboxylate (40.94 g) in pyridine (411 mL), hydroxylamine monohydrochloride (28.56 g) was added at 0° C. and the mixture was stirred at room temperature for 17 hours. The reaction mixture was added to a mixture of AcOE (1.5 L) and hydrochloric acid (2 L, 3.0 N). The organic layer was separated, washed with saturated aqueous sodium bicarbonate (1 L), dried (MgSO4), filtered and concentrated to give the titled compound (39.78 g, colorless solid.)

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium bicarbonate (1 L)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c0f90933b1e4bd984f338bc22ecc4e6
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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