Hydrazine → (4aS,6R,7aS)-2-(4-Methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-amine

HRID 447588Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][C@H:13]3[CH2:15][C@H:16]([N:18]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:17][C@H:12]3[CH2:11][O:10]2)=[CH:5][CH:4]=1.NN>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[O:14][C@H:13]3[CH2:15][C@H:16]([NH2:18])[CH2:17][C@H:12]3[CH2:11][O:10]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-1H-isoindole-1,3(2H)-dione (390. mg, 1.03 mmol), EtOH (11.3 mL) and hydrazine (0.0362 mL, 1.13 mmol) was stirred at 90° C. for 18 h. The resulting mixture was purified via silica gel chromatography eluting with a gradient of 10 to 50% MeOH in DCM. LC/MS: Rt=1.08 min, ES+ 250. (AA standard).

Workup

customThe resulting mixture was purified via silica gel chromatography
washeluting with a gradient of 10 to 50% MeOH in DCM

Sources & evidence

ORD record: ord-3f3b8c16c4f143aa81e865d4878e5ba6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481550B2

Reaction notes

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