Acetic Acid → HCID 9929531, compound

HRID 1290303Notes

Reaction equation

HRID 1290303 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[CH3:10].C([O:34][N+:35]([O-])=[O:36])(C)C.C(O)(=O)C>C(O)(C)(C)C.ClCCl>[OH:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[C:19]([N+:35]([O-:36])=[O:34])[C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 15575Isopropyl nitrateHCID 11142115HCID 11142115, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9929531HCID 9929531, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (1.70 g, 15 mM), (20S)-20-hydroxymethylpregn-4-en-3-one (1.65 g, 5mM) are mixed in tert-butanol and heated at reflux temperature, under argon atmosphere for 90 minutes. The combination is then cooled to room temperature and treated with one continuous portion of isopropylnitrate (0.51 mL, SmM). After 18 hours, the contents of the reaction vessel are acidified with 5 ml of acetic acid, and subsequently diluted with dichloromethane. The solids are then removed by filtration and further washed with additional dichloromethane. The filtrate and wash residue are purified as described in Example 1 to give a crystallized (20S)-20-hydroxymethyl-4-nitropregn-4 -en-3 -one.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature
  3. waitAfter 18 hours
  4. customThe solids are then removed by filtration
  5. washfurther washed with additional dichloromethane
  6. washThe filtrate and wash residue
  7. customare purified

Sources & evidence

ORD record
ord-1b7dacb07bd1450da846a2899ede9602
Source dataset
uspto-grants-1998_05
Patent number
US05750744

Reaction notes

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