tert-Butoxy bis(dimethylamino)methane → 16-Dimethylaminomethylene-3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one

HRID 1156045Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:8]([C@H:9]4[C@@:13]([CH2:16][CH2:17]3)([CH2:14][CH3:15])[C:12](=[O:22])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[CH3:23][N:24]([CH:26](N(C)C)OC(C)(C)C)[CH3:25]>C(O)C>[CH3:23][N:24]([CH:26]=[C:11]1[CH2:10][C@H:9]2[C@H:8]3[C@H:18]([CH2:17][CH2:16][C@:13]2([CH2:14][CH3:15])[C:12]1=[O:22])[C:19]1[CH:20]=[CH:21][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:6][CH2:7]3)[CH3:25]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 10 g of 3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one and 15 g of bis(dimethylamino)tert.-butoxymethane is stirred for 3 hours at 160° C. After cooling the mixture is combined with 50 ml of ethanol and left at -5° C. for crystallizing purposes. After filtering off and drying, 10.6 g of 16-dimethylaminomethylene-3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one is obtained, m.p. 157°-159° C.

Workup

temperatureAfter cooling the mixture
waitleft at -5° C.
customfor crystallizing purposes
filtrationAfter filtering off
customdrying

Sources & evidence

ORD record: ord-081aed428f294c768b0faacee172379b
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04333928

Reaction notes

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