Lithium Chloride → HCID 67745431, compound

HRID 1735416Notes

Reaction equation

HRID 1735416 reaction equation
[Cl-].[Li+].[BH4-].[Na+].C([O:7][C:8]([CH2:10][CH:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])[OH:12])=O)C>C1COCC1.C(O)C>[OH:12][CH:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([NH:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])=[O:19])[CH2:10][CH2:8][OH:7]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 67745442HCID 67745442, compound

Product 1

HCID 67745431HCID 67745431, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Lithium chloride (0.678 g) and sodium borohydride (0.605 g) were added to a solution of (S)-2-[[(S)-2-[2-(ethoxycarbonyl)1-hydroxyethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (3.36 g) in THF-ethanol (1:1, 50 ml), under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered with suction, and the filtrate was concentrated. The residue was dissolved in chloroform, and poured into ice water for separation. The aqueous layer was saturated with sodium chloride and extracted with chloroform. The combined organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (2.50 g).

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered with suction
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in chloroform
  5. additionpoured into ice water for separation
  6. extractionextracted with chloroform
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-04ba7c204c8e4bde932257043f0018e3
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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