Aluminium lithium hydride → HCID 22614988, compound

HRID 843133Notes

Reaction equation

HRID 843133 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[O:18][C:19]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][C:33]5[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=5)[C:20]=4[C:21]=3[CH3:22])=[CH:11][C:9]=2[CH:10]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:22][C:21]1[C:20]2[C:23]([O:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)=[CH:24][CH:25]=[CH:26][C:19]=2[O:18][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:8]2[O:7][C:6]([CH2:4][OH:3])=[CH:10][C:9]=2[CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68655164HCID 68655164, compound

Product 1

HCID 22614988HCID 22614988, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound in Example 36 (10 mg, 0.02 mmol) in THF was added LiAlH4 (1.5 mg) at 0° C. After stirring for 20 min., the reaction was quenched by adding H2O. Silica gel column chromatography (CH2Cl2/MeOH=20/1) gave desired product as a colorless oil. (9 mg, 98%). FAB-MS: m/z 473 (MH+); 1H-NMR (CDCl3): δ 2.04 (2H, m), 2.28 (3H, s), 2.86 (2H, t, J=7.5 Hz), 3.82 (2H, s), 4.14 (2H, t, J=5.5 Hz), 4.75 (2H, s) 5.11 (2H, s), 6.59 (1H, d, J=8 Hz), 6.95(1H, d, J=2 Hz), 7.06 (1H, d, J=8 Hz), 7.12-7.19 (2H, m), 7.34 (1H, d, J=9 Hz), 7.66 (1H, d, J=8 Hz), 8.44 (1H, brd, J=4.5 Hz), 8.51 (1H, brs).

Workup

  1. customat 0° C
  2. customthe reaction was quenched
  3. additionby adding H2O

Sources & evidence

ORD record
ord-129d0b67271d4526a45cdbe37663ffc4
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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