HCID 66910124, compound → HCID 66910127, compound

HRID 910606Notes

Reaction equation

HRID 910606 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([NH:5][C:6](=[O:22])[C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.C[Si](C)(C(C)(C)C)O[C@H]1CC[C@@]2(C)C(C(=O)C[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2O[Si](C)(C)C(C)(C)C)C1.C[Si](C)(C(C)(C)C)O[C@@H]1CC[C@@]2(C)C(C(=O)C[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2O[Si](C)(C)C(C)(C)C)C1>>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([C:6](=[O:22])[NH:5][CH:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]4)[C@@H:8]1[CH2:9][CH2:10][C:11]2=[O:21]

Participants

4

Reactant 3

HCID 66910124HCID 66910124, compoundHCID 66910132HCID 66910132, compoundHCID 66910174HCID 66910174, compound

Product 1

HCID 66910127HCID 66910127, compoundYield 75%

Procedure

6-Azaandrostane-3,7,17-trione was prepared from 3β-hydroxy-6-azaandrostane-7,17-dione by the procedure described above for the preparation of 3β,17β-di(dimethyltert-butylsilyloxy)androstane-6-one and 3α,17β-di(dimethyltert-butylsilyloxy)androstane-6-one (Prepn. 12). The mixture was stirred for 35 minutes, then SiO2 was added and evaporated to dryness. The mixture was purified by flash chromatography (SiO2, acetone/toluene 1/1) to give 6-azaandrostane-3,7,17-trione (75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.34 (s, 1H), 3.31 (dd, 1H), 2.57-1.07 (m, 17H), 0.99 (s, 3H), 0.83 (s, 3H).

Workup

  1. additionSiO2 was added
  2. customevaporated to dryness
  3. customThe mixture was purified by flash chromatography (SiO2, acetone/toluene 1/1)

Sources & evidence

ORD record
ord-659d52931fb94b01b0443396b89c96bd
Source dataset
uspto-grants-2011_09
Patent number
US08022203B2

Reaction notes

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