Sodium → HCID 86598909, compound

HRID 456757Notes

Reaction equation

HRID 456757 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([O:17][CH2:18][C@@H:19]([OH:22])CO)[CH2:14]2)[N:11]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:9])#[N:2].[Na]>CO.O.C(OCC)(=O)C>[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([O:17][CH2:18][CH:19]=[O:22])[CH2:14]2)[N:11]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:9])#[N:2]

Participants

6

Reactant 2

HCID 5360545SodiumHCID 86598910HCID 86598910, compound

Product 1

HCID 86598909HCID 86598909, compoundYield 103.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-{[(2S)-2,3-dihydroxypropyl]oxy}-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 23–1 (250 mg) in methanol (5 mL) and water (5 mL), was added sodium periodinate (522 mg). The mixture was stirred at room temperature for 20 minutes. The reaction mixture was diluted with ethyl acetate, and washed successively with water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo to give the target compound (238 mg). This compound was used immediately without purification.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-d82fca5070894207812bc3e81fdae4ef
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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