Sodium sulfate decahydrate → 1-[4-(benzylthio)tetrahydro-2H-pyran-4-yl]methanamine

HRID 1994702Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:14][C:15]1([CH2:21][N+:22]([O-])=O)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.O1CCCC1>[CH2:7]([S:14][C:15]1([CH2:21][NH2:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of lithium aluminum hydride (2.23 g) and diethyl ether (120 ml) was added a solution of 4-(benzylthio)-4-(nitromethyl)tetrahydro-2H-pyran (5.35 g) in diethyl ether (30 ml) and tetrahydrofuran (15 ml) at 0° C., and the reaction mixture was stirred at 50° C. for 2 hr. The reaction mixture was ice-cooled, sodium sulfate 10 hydrate (19.33 g) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was dried (MgSO4), and the inorganic salt was removed by filtration. The filtrate was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound (3.20 g, yield 67%) as a yellow oil from a fraction eluted with ethyl acetate-methanol (3:1, volume ratio).

Workup

temperaturecooled
stirringthe mixture was stirred overnight at room temperature
dry with materialThe reaction mixture was dried (MgSO4)
customthe inorganic salt was removed by filtration
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-f8f0c3b99ff74374bd56df0924255f80
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652133B2

Reaction notes

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