3-Methylbutanal → HCID 70479527, compound

HRID 615190Notes

Reaction equation

HRID 615190 reaction equation
[C:1]([BH3-])#N.[Na+].CC(C)CC=O.Cl.[OH:12][C@H:13]1[CH2:30][C@@:29]2([CH3:31])[C@@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[C@H:27]([NH:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:26][C@@:24]2([CH3:25])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C:38]([OH:40])=[O:39])[CH2:15][C@@H:14]1[OH:41]>C(O)C.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[OH:12][C@H:13]1[CH2:30][C@@:29]2([CH3:31])[C@@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[C@H:27]([NH:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:26][C@@:24]2([CH3:25])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C:38]([O:40][CH3:1])=[O:39])[CH2:15][C@@H:14]1[OH:41]

Participants

7

Reactant 3

HCID 115523-MethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 70479606HCID 70479606, compound

Product 1

HCID 70479527HCID 70479527, compoundYield 29.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium cyanoborohydride (2.0 g) and 3-methylbutanal (2.8 ml) were added to a solution of Intermediate 2 (2.0 g) in ethanol (30 ml) and the mixture stirred for 18 h. The mixture was diluted with NaHCO3 solution and extracted with ethyl acetate (3×). The extract was washed with water (1×), dried and evaporated to give a foam. This was dissolved in ethyl acetate and extracted with dilute hydrochloric acid (3×) and water (1×). These aqueous extracts were brought to pH 10 by the addition of 0.88 NH3 solution and then extracted with ethyl acetate (3×). This extract was washed with water, dried, filtered and evaporated to give a foam. This was purified by column chromatography eluted with chloroform/methanol (9:1) to give a foam which was crystallised from ethyl acetate to give the title compound (565 mg), m.p. 159°-161°, [α]D +24.2°.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe extract was washed with water (1×)
  3. customdried
  4. customevaporated
  5. customto give a foam
  6. extractionextracted with dilute hydrochloric acid (3×) and water (1×)
  7. additionThese aqueous extracts were brought to pH 10 by the addition of 0.88 NH3 solution
  8. extractionextracted with ethyl acetate (3×)
  9. washThis extract was washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. customto give a foam
  14. customThis was purified by column chromatography
  15. washeluted with chloroform/methanol (9:1)
  16. customto give a foam which
  17. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-1b082fc657324c81b153d978af1f01db
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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