Ammonia → trans-1-Boc-3-cyano-4-hydroxypyrrolidine

HRID 1162701Notes

Reaction equation

HRID 1162701 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]#[N:14])[C@H:10]([O:15]C(=O)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([OH:15])[C@H:11]([C:13]#[N:14])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68647086HCID 68647086, compound

Product 1

HCID 58748337trans-1-Boc-3-cyano-4-hydroxypyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

80.1 A solution of (3S,4S)-3-acetoxy-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g, prepared according to example 79.2) in 10 ml of a 2M NH3 solution in MeOH was stirred at 22° C. for 1 h and evaporated. The residue was chromatographed on silica (heptane/AcOEt, 2.5:1) to give (3S,4S)-3-cyano-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester. Colorless solid. MS 213.3 ([M+H]+)

Workup

  1. customevaporated
  2. customThe residue was chromatographed on silica (heptane/AcOEt, 2.5:1)

Sources & evidence

ORD record
ord-720cff8d04fa4f9d9134f429a236a9f1
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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