Water → HCID 23456565, compound

HRID 1680507Notes

Reaction equation

HRID 1680507 reaction equation
C[O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]2[C:14](=[O:18])[NH:15][CH2:16][CH2:17][N:6]12)=O.[BH4-].[Li+].O.[H-]>O1CCCC1>[OH:2][CH2:3][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]2[C:14](=[O:18])[NH:15][CH2:16][CH2:17][N:6]12

Participants

6

Reactant 4

HCID 962WaterHCID 166653HydrideHCID 4148881Lithium borohydrideHCID 12901822HCID 12901822, compound

Product 1

HCID 23456565HCID 23456565, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2,3,4,6,10b-hexahydro-1-oxo-pyrazino[2,1-a]isoindole-6-carboxylic acid methyl ester (0.5 g, described in Example 24) and lithium borohydride (0.044 g) in tetrahydrofuran (25 ml) is refluxed for 18 hr. Water is carefully added to decompose the excess hydride and the tetrahydrofuran is evaporated. Water is added and the solution is continuously extracted with ethyl acetate for 18 hr. The extract is dried and evaporated to give 1,2,3,4,6,10b-hexahydro-6-hydroxymethylpyrazino[2,1-a]isoindol-1-one (0.245 g), nmr (CDCl3) δ2.8(s), 3.2(m), 3.75(m), 4.3(m), 4.9(m), 6.95(s) and 7.2(m).

Workup

  1. temperatureis refluxed for 18 hr
  2. customthe tetrahydrofuran is evaporated
  3. additionWater is added
  4. extractionthe solution is continuously extracted with ethyl acetate for 18 hr
  5. customThe extract is dried
  6. customevaporated

Sources & evidence

ORD record
ord-5b2145fbe4f34343bcfd55c56312fd20
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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