2-(O-aminooxy)ethylamine dihydrochloride → HCID 86651471, compound

HRID 1912653Notes

Reaction equation

HRID 1912653 reaction equation
[CH2:1]=[C:2]1[CH:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=O)[CH2:18]2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[ClH:23].Cl.[NH2:25][CH2:26][CH2:27][O:28][NH2:29]>>[ClH:23].[NH2:25][CH2:26][CH2:27][O:28][N:29]=[C:17]1[CH2:16][CH2:15][C@@:14]2([CH3:21])[CH:19]([C:2](=[CH2:1])[CH2:3][C@@H:4]3[C@@H:13]2[CH2:12][CH2:11][C@@:9]2([CH3:10])[C@H:5]3[CH2:6][CH2:7][C:8]2=[O:22])[CH2:18]1

Participants

3

Reactant 2

HCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 67536381HCID 67536381, compound

Product 1

HCID 86651471HCID 86651471, compoundYield 40%

Procedure

Prepared in 40% yield as described in Example 1 starting from 6-methyleneandrostane-3,17-dione (II-ah, Prepn. 8) and 2-aminoethoxyamine dihydrochloride. The crude product (1.65 g) was crystallized twice from EtOAc to give the title compound I-ai. H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.97 (bb, 3H), 4.81 (bs, 1H), 4.49 (bs, 1H), 4.08 (t, 2H), 3.10 (m, 1H), 3.02 (t, 2H), 2.45-0.85 (m, 19H), 0.77 (s, 3H), 0.75 (s, 3H).

Workup

  1. customPrepared in 40% yield
  2. customThe crude product (1.65 g) was crystallized twice from EtOAc

Sources & evidence

ORD record
ord-848edfbe4a3c4d86b1dcec0dbd62ad99
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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