Methanol → HCID 86749597, compound

HRID 1733909Notes

Reaction equation

HRID 1733909 reaction equation
[C:1]([N:9]1[CH2:18][CH2:17][C@H:16]2[C@@H:11]([CH2:12][CH2:13][C:14]([OH:27])([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH2:15]2)[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(Cl)(Cl)Cl.CO>C1COCC1>[CH2:1]([N:9]1[CH2:18][CH2:17][C@H:16]2[C@@H:11]([CH2:12][CH2:13][C:14]([OH:27])([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[CH2:15]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 21226445Aluminium lithium hydrideHCID 86749598HCID 86749598, compound

Product 1

HCID 86749597HCID 86749597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure described in Example 49, trans-2-benzoyl-6-hydroxy-6-(4'-methoxyphenyl)decahydroisoquinoline (219 mg, 0.6 mmol) and lithium aluminum hydride (0.14 g, 3.6 mmol) were reacted in anhydrous THF (10 mL). Column chromatography (chloroform: methanol::9:1) afforded the product, a solid (158 mg): mp 38°-40° C.; NMR (CDCl3, 200 MHz): 7.4 (d, 2H, J=8), 7.35-7.2 (m, 5H), 6.85 (d, 2H, J=8), 3.8 (s, 3H), 3.55 (s, 2H), 2.95 (br d, 1H, J=10), 2.85 (br d, 1H, J=10), 2.05 (br t, 1H, J=8), 1.85-1.7 (m, 4H), 1.6-1.3 (m, 7H); HRMS: Calcd: 351.2198, Found: 351.2193.

Sources & evidence

ORD record
ord-bc0834160d354bf99812b49d7a9e583b
Source dataset
uspto-grants-1996_07
Patent number
US05532243

Reaction notes

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