3-Methylbutanal → HCID 18595991, compound

HRID 615187Notes

Reaction equation

HRID 615187 reaction equation
[NH2:1][C@@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[C:20]([O:22][CH3:23])=[O:21])[C@H:12]2[C@H:3]1[C@:4]1([CH3:24])[CH:9]([CH2:10][CH2:11]2)[CH2:8][CH:7]=[CH:6][CH2:5]1.[CH:25](=O)[CH2:26][CH:27]([CH3:29])[CH3:28].[BH4-].[Na+]>CO>[CH3:28][CH:27]([CH3:29])[CH2:26][CH2:25][NH:1][C@@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[C:20]([O:22][CH3:23])=[O:21])[C@H:12]2[C@H:3]1[C@:4]1([CH3:24])[C@@H:9]([CH2:10][CH2:11]2)[CH2:8][CH:7]=[CH:6][CH2:5]1

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 4311764Sodium borohydrideHCID 70480233HCID 70480233, compound

Product 1

HCID 18595991HCID 18595991, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 11α-amino-androst-2-ene-17β-carboxylate (1.46 g) was dissolved in methanol (20 ml) and isovaleraldehyde (1.29 ml) was added in three portions. After stirring for 1 h at room temperature sodium borohydride (0.45 g) was added in several portions to avoid excessive gas evolution and the reaction mixture was stirred for 1/2 h. The methanol was removed at reduced pressure and the residual gum was partitioned between ethyl acetate and water. The layers were separated and the organic phase was washed with M--H2SO4, water and saturated brine, dried and concentrated to about 15 ml. Petrol was added to incipient cloudiness and the solution was allowed to crystallise to give the title compound (1.15 g), m.p. 150°-152° C.

Workup

  1. additionwas added in several portions
  2. customThe methanol was removed at reduced pressure
  3. customthe residual gum was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. washthe organic phase was washed with M
  6. dry with materialH2SO4, water and saturated brine, dried
  7. concentrationconcentrated to about 15 ml
  8. additionPetrol was added to incipient cloudiness
  9. customto crystallise

Sources & evidence

ORD record
ord-a83637b755284ea1b0d1a642a07856a6
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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