Acetic Acid → HCID 89396864, compound

HRID 2171594Notes

Reaction equation

HRID 2171594 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C@@H:3]1[C:7]([O:9][CH3:10])=[O:8].[N:11]([O-])=[O:12].[Na+].C(O)(=O)C>O.C(OCC)(=O)C>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([N:11]=[O:12])[C@@H:3]1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 15381006HCID 15381006, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 89396864HCID 89396864, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3S)-methyl 3-hydroxypyrrolidine-2-carboxylate (16 g, 0.110 moles) in water (60 mL) was added NaNO2 (16 g, 0.220 moles) in water (30 mL) followed by the addition of glacial acetic acid (9.43 mL, 0.165 moles) at 0° C. and the reaction mixture was stirred for 4 h. Once the starting material had disappeared (monitored by TLC), the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated to get the title compound which was used in the next step without purification.

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fcb53db0e5a24a9481c3912aa0a7135e
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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