Acetamide, 2-(trimethylsilyl)- → 3beta,17beta,19-Tri(trimethylsiloxy)androst-4-ene

HRID 371813Notes

Reaction equation

HRID 371813 reaction equation
[CH3:1][C@:2]12[CH2:20][CH2:19][C@H:18]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH2:16][OH:17])[CH2:14][CH2:13][C@H:12]([OH:21])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:22].C[Si:24]([CH2:27]C(N)=O)([CH3:26])[CH3:25]>N1C=CC=CC=1>[CH3:25][Si:24]([CH3:27])([CH3:26])[O:21][C@H:12]1[CH2:13][CH2:14][C@@:15]2([CH2:16][O:17][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:10]([CH2:9][CH2:8][C@@H:7]3[C@@H:18]2[CH2:19][CH2:20][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C@@H:3]2[O:22][Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:11]1

Participants

4

Reactant 2

HCID 357676Acetamide, 2-(trimethylsilyl)-HCID 705847924-Androstene-3beta,17beta,19-triol

Product 1

HCID 228032683beta,17beta,19-Tri(trimethylsiloxy)androst-4-ene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Androst-4-ene-3β,17β,19-triol is dissolved in dry pyridine and trimethylsilylacetamide added thereto. The reaction is completed at room temperature within a few minutes. The pyridine is removed under reduced pressure and the residue purified from an acetone-hexane solution to yield the desired 3β,17β,19-tri(trimethylsiloxy)androst-4-ene.

Workup

  1. waitThe reaction is completed at room temperature within a few minutes
  2. customThe pyridine is removed under reduced pressure
  3. customthe residue purified from an acetone-hexane solution

Sources & evidence

ORD record
ord-dbc2d24b0ed64bcba579f15a7133855b
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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