Aluminium lithium hydride → (+)-(3R)-3-(2-Methoxy-3-methoxymethoxymethylpyridin-4-yl)-pentane-1,3-diol

HRID 2086346Notes

Reaction equation

HRID 2086346 reaction equation
[CH2:1]([C@:3]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH3:15])[C:9]=2[CH2:16][O:17][CH2:18][O:19][CH3:20])[O:5][CH:4]1[CH2:6][OH:7])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:15][O:14][C:10]1[C:9]([CH2:16][O:17][CH2:18][O:19][CH3:20])=[C:8]([C@@:3]([OH:5])([CH2:1][CH3:2])[CH2:4][CH2:6][OH:7])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86587680(+)-(3R)-[3-Ethyl-3-(2-Methoxy-3-methoxymethoxymethyl-pyridin-4-yl)oxiranyl]methanol

Product 1

HCID 12094182(+)-(3R)-3-(2-Methoxy-3-methoxymethoxymethylpyridin-4-yl)-pentane-1,3-diolYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure in Example 6, the reaction was carried out with 6b (0.71 g, 2.5 mmol) and LAH in dry ether (50 nmL) for 24 h to afford 7b as colorless oil (0.54 g, 76%). The crude product was sufficiently pure for the subsequent reaction. IR (CH2Cl2, NaCl,cm−1) 3391, 3056, 2984, 1593, 1446, 1382, 1265, 1037, 743, 546; 1H NMR (300 MHz, CDCl3) δ0.79 (t, J=7.3 Hz, 3H), 1.91 (q,J=7.3 Hz, 2H), 2.15 (m, 2H), 3.42 (s, 3H), 3.60 (m, 1H), 3.74 (m, 1H), 3.98 (s, 3H), 4.71 (s, 2H), 4.89 (d, J=10.7 Hz, 1H), 5.10 (d, J=10.7 Hz, 1H), 6.77 (d,J=5.5 Hz, 1H), 8.05 (d, J=5.5 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ7.81, 36.65, 43.80, 54.14, 55.94, 60.20, 61.13, 80.93, 96.53, 116.33, 117.94, 146.17, 156.45, 163.82; HRMS (EI) m/z calcd for C14H24NO5 (M++H) 286.1654, found 286.1658; LRMS (EI) m/z 286 (M++H, 39), 235(23), 222(86), 205(52), 194(74), 178(100), 150(49), 92(30), 77(15); [α]D23=+0.185 (c=1.08, CH2Cl2).

Sources & evidence

ORD record
ord-4bf0b6ea88ee4aacb4cd1310dbd6cf4e
Source dataset
uspto-grants-2004_04
Patent number
US06723853B2

Reaction notes

Loading…