Lithium borohydride → HCID 53921892, compound

HRID 892607Notes

Reaction equation

HRID 892607 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:24])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:23])[CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22].[BH4-].[Li+].C(O)(=O)C.CO>C1COCC1.C(O)C>[O:22]=[C:18]1[CH2:19][CH2:20][CH2:21][N:17]1[CH2:16][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[CH2:3][OH:2])=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 4148881Lithium borohydrideHCID 10129899Acetic acid methanolHCID 54258508HCID 54258508, compound2×

Product 1

HCID 53921892HCID 53921892, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N-[(2-Oxo-1-pyrrolidinyl)acetyl]-L-prolyl-L-proline methyl ester (Compound 1) (2.56 g) as obtained in Example 1 was dissolved in a mixture of THF (30 ml) and ethanol (6 ml), to which was added a THF solution of 2 M lithium borohydride (7.3 ml) under ice-cooling. After 3 hours' stirring at room temperature, a 50% acetic acid-methanol solution was added to adjust the pH of the mixture to 6. The residue obtained by concentration was purified by silica gel column chromatography (chloroform-methanol) to give 2.02 g of N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-prolyl-L-prolinol.

Workup

  1. temperaturecooling
  2. customThe residue obtained by concentration
  3. customwas purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-a2e7813f90494cb68597817356162b80
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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