Aluminium lithium hydride → 1-(4-{4-[(3-pyrrolidin-1-ylpropyl)thio]phenyl}tetrahydro-2H-pyran-4-yl)methanamine

HRID 273013Notes

Reaction equation

HRID 273013 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[N:1]1([CH2:6][CH2:7][CH2:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][NH2:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 598374854-{4-[(3-pyrrolidin-1-ylpropyl)thio]phenyl}tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 685766791-(4-{4-[(3-pyrrolidin-1-ylpropyl)thio]phenyl}tetrahydro-2H-pyran-4-yl)methanamineYield 91%

Procedure

The title compound (2.42 g, 91%) was prepared using 4-{4-[(3-pyrrolidin-1-ylpropyl)thio]phenyl}tetrahydro-2H-pyran-4-carbonitrile and lithium aluminium hydride similarly to the procedure used for intermediate 51. LRMS APCI+ m/z 335 [MH]+. Microanalysis: Found: C, 64.08; H, 8.79; N, 7.447%. C19H30N2OS.0.33DCM requires C, 64.04; H, 8.52; N, 7.73%.

Sources & evidence

ORD record
ord-418bee775bcd453192c1d3040ae4dd4d
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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