2-(O-aminooxy)ethylamine dihydrochloride → (1S,2R,5E,7S,9S,11S,12S,15S,16S)-5-(2-aminoethoxyimino)-2,6,6,16-tetramethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-15-ol;hydrochloride

HRID 1182861Notes

Reaction equation

HRID 1182861 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@H:5]3[C@@H:14]([C@@:15]4([CH3:23])[CH2:16][CH2:17][C:18](=O)[C:19]([CH3:21])([CH3:20])[C@:2]124)[CH2:13][CH2:12][C@@:10]1([CH3:11])[C@H:6]3[CH2:7][CH2:8][C@@H:9]1[OH:24].[ClH:25].Cl.[NH2:27][CH2:28][CH2:29][O:30][NH2:31]>>[ClH:25].[NH2:27][CH2:28][CH2:29][O:30]/[N:31]=[C:18]1/[C:19]([CH3:21])([CH3:20])[C@:2]23[O:1][C@H:3]2[CH2:4][C@@H:5]2[C@@H:14]([C@@:15]3([CH3:23])[CH2:16][CH2:17]/1)[CH2:13][CH2:12][C@@:10]1([CH3:11])[C@H:6]2[CH2:7][CH2:8][C@@H:9]1[OH:24]

Participants

3

Reactant 2

HCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 866491775alpha,6alpha-Epoxy-17beta-hydroxy-4,4-dimethylandrostan-3-one

Product 1

HCID 87552587(1S,2R,5E,7S,9S,11S,12S,15S,16S)-5-(2-aminoethoxyimino)-2,6,6,16-tetramethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-15-ol;hydrochlorideYield 68%

Procedure

The title compound was prepared as described in Example 2 starting from 5α,6α-epoxy-17β-hydroxy-4,4-dimethylandrostan-3-one, (Preparation 8, 54 mg) and 2-aminoethoxyamine dihydrochloride (97 mg). The solution was evaporated, water was added and the aqueous phase was extracted with THF. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was triturated with diisopropyl ether/MeOH 95/5 and the precipitate was filtered to give the title compound (47 mg, 68%).

Workup

  1. customThe title compound was prepared
  2. customThe solution was evaporated
  3. additionwater was added
  4. extractionthe aqueous phase was extracted with THF
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe crude product was triturated with diisopropyl ether/MeOH 95/5
  9. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-597afe01547b41a1b00db255228a5c2d
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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