Hydrochloric Acid → HCID 15907974, compound

HRID 2224046Notes

Reaction equation

C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@:8]([CH3:22])([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.CC(C[AlH]CC(C)C)C.C(O)C.Cl>C1(C)C=CC=CC=1.C(O)C.O>[CH3:22][C@@:8]12[CH2:7][CH2:6][C:5]3[CH:4]=[C:3]([OH:2])[CH:20]=[CH:19][C:18]=3[C@H:17]1[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[OH:21]

Participants

Conditions

Temperature: 0 °C

Procedure

74 mg of 3-methoxy-8β-methyl-estra-1,3,5(10)-trien-17β-ol was dissolved in 3 ml of anhydrous toluene, cooled to 0° C. and mixed carefully under argon with 0.6 ml of DIBAH. The reaction mixture was slowly refluxed, and it was kept at this temperature for 3.5 hours. Then, it was cooled again to 0° C., the solution was mixed in succession with 2 ml of ethanol, 2 ml of ethanol-water mixture (v/v=1/1) and 2 ml of semi-concentrated hydrochloric acid and extracted several times with ethyl acetate. The collected organic phases were washed neutral with water, dried with magnesium sulfate and evaporated to the dry state in a vacuum. 70 mg (99%) of colorless crystals with a melting point of 168-170° C. was obtained.

Workup

temperatureThe reaction mixture was slowly refluxed
temperatureThen, it was cooled again to 0° C.
extractionextracted several times with ethyl acetate
washThe collected organic phases were washed neutral with water
dry with materialdried with magnesium sulfate
customevaporated to the dry state in a vacuum

Sources & evidence

ORD record: ord-92c085887a22438db59bfc0a6e1022ec
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378404B2

Reaction notes

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