1-Propanol → HCID 70479025, compound

HRID 615194Notes

Reaction equation

HRID 615194 reaction equation
[OH:1][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C@H:16]([NH:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:27]([O:29][CH3:30])=[O:28])[CH2:4][C@@H:3]1[OH:31].S(=O)(=O)(O)O.[CH2:37](O)[CH2:38]C>>[OH:1][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C@H:16]([NH:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:27]([O:29][CH2:30][CH2:37][CH3:38])=[O:28])[CH2:4][C@@H:3]1[OH:31]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 70479527HCID 70479527, compound

Product 1

HCID 70479025HCID 70479025, compound

Procedure

A solution of methyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (437 mg) in propan-1-ol (30 ml) was heated at 100° C. with conc. sulphuric acid (0.2 ml) for 40 h. The cooled mixture was concentrated by evaporation and the residue diluted with water (150 ml) and brought to pH 10 by the addition of 0.88 ammonia solution. The suspension was extracted with ethyl acetate (3×) and the extracts washed with brine, dried and evaporated to give a solid. This was crystallised from ethyl acetate to give the title compound (70 mg), m.p. 140°-142° C., [α]D +17.2°.

Workup

  1. concentrationThe cooled mixture was concentrated by evaporation
  2. additionthe residue diluted with water (150 ml)
  3. additionbrought to pH 10 by the addition of 0.88 ammonia solution
  4. extractionThe suspension was extracted with ethyl acetate (3×)
  5. washthe extracts washed with brine
  6. customdried
  7. customevaporated
  8. customto give a solid
  9. customThis was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-05c7e891e6e24ad486b5695f437f5baf
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

Loading…