Water → HCID 12961956, compound

HRID 1065694Notes

Reaction equation

HRID 1065694 reaction equation
B#B.C(O)(=O)C.C([O:10][C@H:11]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][C@@H:19]([O:32]C(=O)C)[C:20]2=[N:30]O)[CH2:12]1)(=O)C.O>O1CCCC1>[NH2:30][C@H:20]1[C@H:19]([OH:32])[CH2:18][C@H:17]2[C@H:16]3[C@H:25]([CH2:24][CH2:23][C@:21]12[CH3:22])[C@:26]1([CH3:29])[C@H:13]([CH2:12][C@@H:11]([OH:10])[CH2:28][CH2:27]1)[CH2:14][CH2:15]3

Participants

5

Reactant 3

HCID 962WaterHCID 6328200DiboronHCID 86738377HCID 86738377, compound

Product 1

HCID 12961956HCID 12961956, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of diborane in tetrahydrofurane (257 ml; 1 M) was added dropwise to a stirred solution of 3β,16α-bis(acetyloxy)-5α-androstan-17-one oxime acetate (11.7 g) in tetrahydrofuran (257 ml) at 0° C. under a nitrogen atmosphere. The solution was set aside at room temperature overnight, then water (35 ml) was carefully added to the cooled (0° C.), stirred solution. Tetrahydrofuran was distilled off and replaced with ethanol (400 ml) and sodium hydroxide solution (12 ml; 4 N), and the solution was heated under reflux for 3 h. The solution was concentrated and cooled; water (100 ml) and concentrated hydrochloric acid (12 ml) were added and the solution was heated on a water bath for 1 h. Aqueous sodium hydroxide (2 N) was then added to the cooled solution to precipitate the product, which was filtered off, washed with water and dried in vacuo to give 17β-amino-5α-androstane-3β,16α-diol (6.7 g), m.p. 234°-237° C. (decomp.), [α]D -3.8° (c 1.1 in MeOH).

Workup

  1. distillationTetrahydrofuran was distilled off
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 3 h
  4. concentrationThe solution was concentrated
  5. temperaturecooled
  6. additionwater (100 ml) and concentrated hydrochloric acid (12 ml) were added
  7. temperaturethe solution was heated on a water bath for 1 h
  8. additionAqueous sodium hydroxide (2 N) was then added to the cooled solution
  9. customto precipitate the product, which
  10. filtrationwas filtered off
  11. washwashed with water
  12. customdried in vacuo

Sources & evidence

ORD record
ord-7c654a9343414abf8a8cdf7be9668120
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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