Tetrahydro-2-(2-propynyloxy)-2H-pyran → (8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-ol

HRID 2057

Reaction equation

HRID 2057 reaction equation
C(O[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)C#C.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14]>CCCCCC.O1CCCC1>[CH3:14][C@:13]12[CH2:12][CH2:11][C@H:5]3[C@@H:5]([CH2:11][CH2:12][C:13]4[C@@H:10]3[CH2:9][CH2:8][CH2:7][CH:14]=4)[C@@H:10]1[CH2:9][CH2:8][C@@H:7]2[OH:6]

Participants

5

Reactant 2

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 252818(8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

As described under 3D, 460 mg of 7G is produced from 442 mg of 7F with 1.30 ml of 2-(2-propinyloxy)tetrahydro-2H-pyrane and 5.36 ml of a 15% solution of butyllithium in hexane in 70 ml of tetrahydrofuran.

Sources & evidence

ORD record
ord-dda6f0d331b14af09fea8960240ce219
Source dataset
uspto-grants-1998_03
Patent number
US05728689

Linked notes

Loading…