Formaldehyde → 3,3-Ethylenedioxy-20-nitropregna-5,16-diene-9alpha,21-diol

HRID 1613968Notes

Reaction equation

HRID 1613968 reaction equation
[CH2:1]=[O:2].C(N(CC)CC)C.[CH2:10]1[CH2:37][O:36][C:12]2([CH2:29][CH2:28][C@@:27]3([CH3:30])[C:14](=[CH:15][CH2:16][C@@H:17]4[C@:26]3([OH:31])[CH2:25][CH2:24][C@@:22]3([CH3:23])[C@H:18]4[CH2:19][CH2:20][C:21]3=[CH:32][N+:33]([O-:35])=[O:34])[CH2:13]2)[O:11]1.O>CC(O)C.C(O)(=O)C>[CH2:37]1[CH2:10][O:11][C:12]2([CH2:29][CH2:28][C@@:27]3([CH3:30])[C:14](=[CH:15][CH2:16][C@@H:17]4[C@:26]3([OH:31])[CH2:25][CH2:24][C@@:22]3([CH3:23])[C@H:18]4[CH2:19][CH:20]=[C:21]3[CH:32]([N+:33]([O-:35])=[O:34])[CH2:1][OH:2])[CH2:13]2)[O:36]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8471TriethylamineHCID 569874143,3-Ethylenedioxy-17-(nitromethylene)androst-5-en-9alpha-ol

Product 1

HCID 542775113,3-Ethylenedioxy-20-nitropregna-5,16-diene-9alpha,21-diolYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Procedure

Under a nitrogen atmosphere formaline (2 ml, 40% solution in water) and triethylamine (1 ml) were added to a stirred suspension of 3,3-ethylenedioxy-17-(nitromethylene)androst-5-en-9α-ol (0.50 g) in 2-propanol (10 ml). After stirring for one hour at room temperature the reaction was found to be complete as evidenced by TLC. The reaction mixture was poured into a mixture of water (200 ml) and acetic acid (3 ml) and stirred for 30 minutes. The resulting precipitate was filtered, washed with water and dried to afford 0.46 g of the title compound (85%). According to NMR the product was a 4:1 mixture of the two C20 diastereomers which were separated by chromotagraphy (silica gel; toluene/acetone 3/1) and analysed.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d574a4fb10f24f0ab263c833f946c18c
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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