(R)-2-aminopropoxyamine dihydrochloride → HCID 178462163, compound

HRID 1912659Notes

Reaction equation

HRID 1912659 reaction equation
[OH:1]/[N:2]=[C:3]1\[CH2:4][C@@H:5]2[C@@H:14]([C@:15]3([CH3:22])[CH:20]\1[CH2:19][C:18](=O)[CH2:17][CH2:16]3)[CH2:13][CH2:12][C@@:10]1([CH3:11])[C@H:6]2[CH2:7][CH2:8][C:9]1=[O:23].[ClH:24].Cl.[NH2:26][C@H:27]([CH3:31])[CH2:28][O:29][NH2:30]>>[NH2:26][C@H:27]([CH3:31])[CH2:28][O:29][N:30]=[C:18]1[CH2:19][CH2:20][C@@:15]2([CH3:22])[CH:16]([CH2:3][CH2:4][C@@H:5]3[C@@H:14]2[CH2:13][CH2:12][C@@:10]2([CH3:11])[C@H:6]3[CH2:7][CH2:8][CH2:9]2)[CH2:17]1.[ClH:24].[OH:1]/[N:2]=[C:3]1\[CH2:4][C@@H:5]2[C@@H:14]([C@:15]3([CH3:22])[CH:20]\1[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:13][CH2:12][C@@:10]1([CH3:11])[C@H:6]2[CH2:7][CH2:8][C:9]1=[O:23]

Participants

3

Reactant 2

HCID 86651490(R)-2-aminopropoxyamine dihydrochlorideHCID 87653583(6E,8R,9S,10R,13S,14S)-6-hydroxyimino-10,13-dimethyl-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

Product 1

HCID 178462163HCID 178462163, compoundYield 93%

Procedure

Prepared as described in Example 1 starting from 6-(E)-hydroxyiminoandrostane-3,17-dione (II-at, Prepn. 20, 500 mg) and (R)-2-aminopropoxyamine dihydrochloride (Prepn. 93, 257 mg). The crude product was crystallized from MeOH/EtOAc to give the title compound as a white solid (503 mg, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.50 (1H, s), 7.98 (3H, m), 3.97 (2H, m), 3.40 (1H, m), 3.11 (0.5H, m), 3.05 (0.5H, m), 2.54-1.15 (22H, m), 0.79 (3H, s), 0.78 (3H, s).

Workup

  1. customPrepared
  2. customThe crude product was crystallized from MeOH/EtOAc

Sources & evidence

ORD record
ord-7128a2081ce945ddbe67d289521040af
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

Loading…