Ammonium Chloride → 15beta-Ethyl-3-methoxy-15beta-methylestra-1,3,5 (10)-trien-17alpha-ol

HRID 1081986Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@@:9]1([CH3:30])[C@H:14]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:12]2([CH3:13])[C:11](=[O:29])[CH2:10]1)[C:23]1[CH:22]=[CH:21][C:20]([O:27][CH3:28])=[CH:19][C:18]=1[CH2:17][CH2:16]3)[CH3:8].[Cl-].[NH4+]>O1CCCC1>[CH3:8][CH2:7][C@:9]1([CH3:30])[C@H:14]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:12]2([CH3:13])[C@H:11]([OH:29])[CH2:10]1)[C:23]1[CH:22]=[CH:21][C:20]([O:27][CH3:28])=[CH:19][C:18]=1[CH2:17][CH2:16]3

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (58 mg; 0.31 mmol) was added to a solution of the 15β-ethyl-15β-methyl ketone (5) (100 mg; 0.31 mmol) in dry tetrahydrofuran (2 ml) at 0°C. The solution was stirred at 0° C. for 5 min. Saturated aqueous ammonium chloride was added and the mixture was filtered. Standard work-up of the filtrate gave 15β-ethyl-3-methoxy-15α-methylestra-1,3,5(10)-trien-17β-ol (13) (92 mg; 90%), as an oil, [α]D +70° (c 1.0); νmax 3604 cm-1 (OH); δH 0.88 (3H, t, J 7.2 Hz, 15β-CH2CH3), 0.90 (3H, s, 15α-Me), 1.10 (3H, s, 13β-Me), 1.51 obsc (2H, m, 15α-CH2CH3), 1.73 obsc (2H, m, 16α- and 16β-H), 2.84 (2H, m, 6-H2), 3.74 (1H, dd, J 9.9 and 8.2 Hz, 17α-H), 3.78 (3H, s, 3-OMe), 6.63 (1H, d, J 2.8 Hz, 4-H), 6.71 (1H, dd, J 8.4 and 2.8 Hz, 2-H), and 7.21 (1H, d, J 8.4 Hz, 1-H); δc 8.6 (C-15 2), 13.9 (C-18), 25.9 (C-151), 28.6 (C-11), 29.0 (C-7), 29.9 (C-6), 30.3 (C-12), 36.8 (C-8), 39.0 (15α-Me), 40.0 (C-15), 45.2 (C-9), 45.5 (C-4), 55.2 (3-OMe), 59.6 (C-13), 79.5 (C-16), 80.0 (C-17), 111.4 (C-2), 113.6 (C-4), 126.2 (C-1), 133.0 (C-10), 137.7 (C-5), and 157.5 (C-3).

Workup

filtrationthe mixture was filtered

Sources & evidence

ORD record: ord-7ba4625355b7461f87fbf817e4827b36
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05587496

Reaction notes

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