Sodium Hydroxide → HCID 53467746, compound

HRID 573803Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[C:19]2[C@H:20]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[O:21][C:22]3([CH2:26][CH2:25][CH2:24][CH2:23]3)[C:18]=2[C:17]2[C:16](=[O:37])[CH2:15][C:14]([CH3:39])([CH3:38])[CH2:13][C:12]=2[N:11]=1)([CH3:9])[CH3:8].[OH-].[Na+]>O1CCCC1.O.C(OC(=O)C)C>[CH:7]([C:10]1[C:19]2[C@H:20]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:31][CH:32]=3)[O:21][C:22]3([CH2:23][CH2:24][CH2:25][CH2:26]3)[C:18]=2[C:17]2[C@@H:16]([OH:37])[CH2:15][C:14]([CH3:39])([CH3:38])[CH2:13][C:12]=2[N:11]=1)([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

120 μl of a 1 M solution of lithium aluminiumhydride in tetrahydrofurane are added dropwise to 55 mg (S)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-7′,8′-dihydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinolin]-9′(6′H)-one in 2 ml tetrahydrofurane at room temperature. The mixture is stirred for 2 hours and then cooled to 0° C. 10 μl water and 10 μl 4 N solution of sodium hydroxide in water are added successively and the mixture is stirred for further 30 minutes. Then the mixture is diluted with ethylacetate and dried with magnesium sulphate. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50).

Workup

stirringthe mixture is stirred for further 30 minutes
dry with materialdried with magnesium sulphate
customThe solvents are evaporated in vacuo
customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50)

Sources & evidence

ORD record: ord-66bd2a1375184d528e15c637611ef177
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029544B2

Reaction notes

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