Hydrochloric Acid → HCID 70048425, compound

HRID 1086280Notes

Reaction equation

HRID 1086280 reaction equation
B.[Na].C[O:4][C:5](=O)[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:29])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:28])[CH2:18][CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1.Cl>O1CCCC1.CO>[CH:19]1([CH2:18][C:17]([N:13]2[CH2:14][CH2:15][CH2:16][C@H:12]2[C:11]([N:7]2[CH2:8][CH2:9][CH2:10][C@H:6]2[CH2:5][OH:4])=[O:29])=[O:28])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 70047932HCID 70047932, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 70048425HCID 70048425, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.57 g of sodium boron hydride was added with stirring to 9 ml of a 80% methanol solution under ice-cooling. To the mixture was added dropwise 1.15 g of 1-[1-(2-indanylacetyl)-L-prolyl]-L-proline methyl ester dissolved in a mixed solution of 5 ml of tetrahydrofuran and 5 ml of methanol. After addition, the mixture was stirred for 15 hours at room temperature. The reaction mixture was acidified by adding diluted hydrochloric acid and extracted with ether. The organic layer obtained was washed with brine and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain 0.73 g of 1-[1-(2-indanylacetyl)-L-prolyl]-L-prolinol as an oily substance. (yield: 68%)

Workup

  1. temperaturecooling
  2. additionAfter addition
  3. extractionextracted with ether
  4. customThe organic layer obtained
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporating the solvent under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6c93980b65944efa8a61c00cde78bed9
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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