Pivaloyl chloride → 7beta-Hydroxy-3beta,15alpha-dipivaloyloxy-5-androsten-17-one

HRID 1903003Notes

Reaction equation

HRID 1903003 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][C@H:6]([OH:23])[C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[C@@H:9]([OH:22])[CH2:10][C:11]2=[O:21])[CH2:3]1.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[OH:23][C@H:6]1[CH:5]=[C:4]2[C@:17]([CH3:20])([CH2:18][CH2:19][C@H:2]([O:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3]2)[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C:11](=[O:21])[CH2:10][C@@H:9]1[O:22][C:11](=[O:21])[C:12]([CH3:14])([CH3:13])[CH3:8]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 45092588(3beta)-3,7,15-Trihydroxyandrost-5-en-17-one

Product 1

HCID 566179167beta-Hydroxy-3beta,15alpha-dipivaloyloxy-5-androsten-17-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

One gram of 3β,7β,15α-trihydroxy-5-androsten-17-one is dissolved at room temperature in 20 ml of pyridine; 2 ml of pivalic acid chloride as well as 100 mg of 4-dimethylaminopyridine are added to the reaction mixture, and the latter is agitated at room temperature for 48 hours. The reaction mixture is then poured into 250 ml of ice water, stirred for 2 hours at room temperature, the resultant precipitate is vacuum-filtered, washed with water, and dried for 8 hours in a vacuum drying cabinet at 50° C., yielding 1.38 g of 7β-hydroxy-3β,15α-dipivaloyloxy-5-androsten-17-one, mp 195°-197° C.

Workup

  1. stirringstirred for 2 hours at room temperature
  2. filtrationthe resultant precipitate is vacuum-filtered
  3. washwashed with water
  4. customdried for 8 hours in a vacuum
  5. customdrying cabinet at 50° C.

Sources & evidence

ORD record
ord-ae2093a34f78490eb090c2d3e77846a0
Source dataset
uspto-grants-1984_03
Patent number
US04435327

Reaction notes

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