Acetonitrile → METHYL (2S)-PYRROLIDIN-2-YLACETATE

HRID 549354

Reaction equation

HRID 549354 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](#N)C.C(N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 688605(S)-2-(1-BOC-2-pyrrolidinyl)acetic acid

Product 1

HCID 11075654METHYL (2S)-PYRROLIDIN-2-YLACETATE

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-2-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2.00 g) in methanol (1.32 ml)/acetonitrile (40 ml) was treated with N,N-diisopropylethylamine (1.78 ml). Trimethylsilyldiazomethane (2M, 8.73 ml) was added dropwise and the resulting mixture was stirred at room temperature, under argon for 24 h. The mixture was diluted with ethyl acetate, washed with 2M HCl, saturated aqueous sodium hydrogen carbonate, brine then dried (magnesium sulfate). The solvent was removed under reduced pressure to afford the title compound (2.10 g)

Workup

  1. washwashed with 2M HCl, saturated aqueous sodium hydrogen carbonate, brine
  2. dry with materialthen dried (magnesium sulfate)
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-67ba47f2c0724598a71ab82276e2df3f
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Linked notes

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