Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate → 5-(4-Chlorobenzyl)-4-(2-hydroxyethyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

HRID 1034260Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:21])[CH2:20][C:9]([C:10]=34)=[C:8]2[CH2:22][C:23](OCC)=[O:24])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:21])[CH2:20][C:9]([C:10]=34)=[C:8]2[CH2:22][CH2:23][OH:24])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of product from Step 3 (785 mg, 1.83 mmol) in THF (30 mL), cooled to 0° C. and under N2 atmosphere, there was added LiAlH4 (152 mg, 4 mmol). The resulting mixture was stirred at 0° C. for 30 minutes, then quenched carefully with ice-cold H2O, and acidified with 1N aq HCl (10 mL). The mixture was extracted twice with Et2O, and these extracts were washed 3× with brine, dried over Na2SO4, and evaporated. The residue was chromatographed, eluting with a 1:1 mixture of EtOAc and hexane, to afford the title product as a thick oil.

Workup

customquenched carefully with ice-cold H2O
extractionThe mixture was extracted twice with Et2O
washthese extracts were washed 3× with brine
dry with materialdried over Na2SO4
customevaporated
customThe residue was chromatographed
washeluting with a 1:1 mixture of EtOAc and hexane

Sources & evidence

ORD record: ord-a47bbad0e9c04504893f39c3cb589083
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314898

Reaction notes

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