Pyridine → HCID 25152414, compound

HRID 1965888Notes

Reaction equation

[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][CH:9]([CH2:11][CH2:12][CH2:13][C@H:14]([C@@H:16]1[C@:34]2([CH3:35])[C@H:19]([C@H:20]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:23]([CH2:24][C@H:25]([CH2:27][CH2:28]2)[OH:26])=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])[CH3:10].N1C=CC=CC=1>C(Cl)Cl>[C:1]([OH:6])(=[O:7])[CH2:2][CH2:3][C:4]([OH:26])=[O:5].[CH3:10][CH:9]([CH2:11][CH2:12][CH2:13][C@H:14]([C@@H:16]1[C@:34]2([CH3:35])[C@H:19]([C@H:20]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:23]([CH2:24][C@H:25]([CH2:27][CH2:28]2)[OH:26])=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])[CH3:8].[CH3:10][CH:9]([CH2:11][CH2:12][CH2:13][C@H:14]([C@@H:16]1[C@:34]2([CH3:35])[C@H:19]([C@H:20]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:23]([CH2:24][C@H:25]([CH2:27][CH2:28]2)[OH:26])=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])[CH3:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Succinic anhydride (1.55 gm, 15.5 mmol) was added to a solution of cholesterol (5 gm, 12.9 mmol) in pyridine (10 ml). After heating at 80° C. for 3 h, the reaction mixture was diluted with DCM and the organic phase was washed with 10% HCl (50 ml) followed by a water wash (50 ml). The organic phase was separated, dried over Na2SO4 to obtain cholesterol hemisuccinate as white solid. The solid was recrystallized from DCM and hexane (5.78 gm, 92% yield, and melting point 176-178° C.). 1H NMR (300 MHz, CDCl3): δ 5.47 (d, vinylic-H, J=5.0), 4.70-4.60 (m, 1H), 2.75-2.65 (m, 4H), 2.38-2.35 (d, 7H), 2.20-1.80 (m, 12H), 1.60-1.40 (m, 12H), 0.78-0.75 (m, 3H).

Workup

washthe organic phase was washed with 10% HCl (50 ml)
washwash (50 ml)
customThe organic phase was separated
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-43edbecf7570418ab491cc3a59fe5221
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420118B2

Reaction notes

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