Citric Acid → HCID 86598911, compound

HRID 456758Notes

Reaction equation

HRID 456758 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][CH:19]=[O:20])[CH2:14]2)[N:11]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:9])#[N:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[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][CH2:19][OH:20])[CH2:14]2)[N:11]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:9])#[N:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 86598909HCID 86598909, compound

Product 1

HCID 86598911HCID 86598911, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-(2-oxoethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 25-1 (238 mg) in methanol (6 mL), was added sodium borohydride (26.2 mg). The mixture was stirred at room temperature for 20 minutes. To the resulting mixture, was added citric acid solution. The mixture evaporated in vacuo. The residue was diluted with ethyl acetate, and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo to give the target compound (220 mg).

Workup

  1. customThe mixture evaporated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d97659b69ca442d0a85c8fbe51b69812
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

Loading…