Aluminium lithium hydride → HCID 59837391, compound

HRID 273015Notes

Reaction equation

HRID 273015 reaction equation
[N:1]1([C:6]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[N:1]1([CH2:6][C:8]2([C:14]3[CH:15]=[CH:16][C:17]([S:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][CH2:27][CH2:28]4)=[CH:18][CH:19]=3)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68578404HCID 68578404, compound

Product 1

HCID 59837391HCID 59837391, compoundYield 27%

Procedure

The title compound (58 mg, 27%) was prepared using 1-[3-({4-[4-(pyrrolidin-1-ylcarbonyl)tetrahydro-2H-pyran-4-yl]phenyl}thio)propyl]pyrrolidine and lithium aluminium hydride similarly to the procedure used for example 142. 1H NMR (400 MHz, CDCl3) δ 1.54-1.57 (m, 4H), 1.75-1.79 (m, 4H), 1.84-1.94 (m, 4H), 2.06-2.10 (m, 2H), 2.18-2.22 (m, 4H), 2.47-2.50 (m, 4H), 2.57 (t, 2H), 2.63 (s, 2H), 2.96 (t, 2H), 3.54 (t, 2H), 3.73-3.78 (m, 2H), 7.22 (d, 2H), 7.29 (d, 2H). HRMS ESI+ m/z 389.2615 [MH]+.

Sources & evidence

ORD record
ord-ec3bece4fe6c4ca2ab7b0bdf836374d8
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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