O-ethylhydroxylamine hydrochloride → (E,2S,5S,6R,14R,15S)-N-ethoxy-2,6-dimethyl-18,21,22,25-tetraoxahexacyclo[15.4.4.01,17.02,15.05,14.06,11]pentacosan-12-imine

HRID 1912688Notes

Reaction equation

HRID 1912688 reaction equation
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16][C:17](=O)[CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.[NH2:29][O:30][CH2:31][CH3:32].Cl>>[CH2:11]1[CH2:10][O:9][C:8]23[O:13][CH2:14][CH2:1][O:2][C:3]2([C@:4]2([CH2:27][CH2:26][C@H:25]4[C@@H:15]([CH2:16]/[C:17](=[N:29]\[O:30][CH2:31][CH3:32])/[CH:18]5[C@:23]4([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:12]1

Participants

3

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 6753591417,17-Bis(ethylendioxy)androstan-6-one

Product 1

HCID 178474300(E,2S,5S,6R,14R,15S)-N-ethoxy-2,6-dimethyl-18,21,22,25-tetraoxahexacyclo[15.4.4.01,17.02,15.05,14.06,11]pentacosan-12-imineYield 90%

Procedure

17,17-Bis(ethylendioxy)-6(E)-ethoxyiminoandrostane was prepared in 90% yield starting from 3,3:17,17-bis(ethylendioxy)androstan-6-one and NH2OCH2CH3.HCl by the procedure described above in Prepn. 21. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.99 (2H, q), 3.92-3.75 (8H, m), 3.25 (1H, dd), 2.25 (1H, m), 1.99-0.94 (18H, m), 1.17 (3H, t), 0.82 (3H, s), 0.75 (3H, s).

Sources & evidence

ORD record
ord-663986fcd0a34e7a874ab5a074042171
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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