HCID 70465682, compound → HCID 57027331, compound

HRID 1284877Notes

Reaction equation

C([O:3][C:4](=O)[C:5]([Cl:44])([CH2:11][C:12]([F:43])([F:42])[CH2:13][C@H:14]([C@@H:16]1[C@:33]2([CH3:34])[C@H:19]([C@H:20]3[C@H:30]([CH2:31][CH2:32]2)[C@:28]2([CH3:29])[C:23]([CH2:24][C@@H:25]([O:35]C4CCCCO4)[CH2:26][CH2:27]2)=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])[C:6](OCC)=[O:7])C>CCOCC>[Cl:44][C:5]([CH2:11][C:12]([F:42])([F:43])[CH2:13][C@H:14]([C@@H:16]1[C@:33]2([CH3:34])[C@H:19]([C@H:20]3[C@H:30]([CH2:31][CH2:32]2)[C@:28]2([CH3:29])[C:23]([CH2:24][C@@H:25]([OH:35])[CH2:26][CH2:27]2)=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])([CH2:6][OH:7])[CH2:4][OH:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the chlorodiester (10) (730 mg, 1.1 mmol) in ether (15 ml) lithium aluminium hydride (48 mg) was added and the mixture was stirred at 0° C. for 1 hr. and then stirred at room temperature for 2 hr. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (50 g). Elution with dichloromethane provided the chlorodiol (11) (250 mg, 39%) mp 152°-153° C. (n-hexane-ether). 1 -H-NMR δ(CDCl3 -acetone d6 -DMSO d6): 0.77 (3H, s, 18-H3), 1.00 (3H, s, 19-H3), 1.10 (3H, d, J=6 Hz, 21-H3), 3.50-4.50 (7H, m, 3-H, 26-H2, 27-H2, and THP), 4.77 (3H, m, 26-OH, 27-OH, and THP), 5.38 (1H, m, 6-H); δ(CDCl3 -acetone d6 -DMSOd6 -D2O): 3.60 (2H, m, THP), 3.77 (4H, s, 26-H2 and 27-H2), 4.77 (1H, m, THP). MS m/z: 434, 416, 404. Anal. Calcd for C32H51O4ClF2 : C, 67.05; H, 8.97; Cl, 6.19; F, 6.63. Found: C, 67.08; H, 8.89; Cl, 5.99; F, 6.53.

Workup

stirringand then stirred at room temperature for 2 hr
extractionThe usual work-up (ether for extraction)
customgave a crude product, which
washElution with dichloromethane

Sources & evidence

ORD record: ord-e8ca2406c6754401b97070b9a9e7c5c9
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04564474

Reaction notes

Loading…