Aluminium lithium hydride → HCID 70201669, compound

HRID 1594580Notes

Reaction equation

HRID 1594580 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[O:8][CH2:9][C@@H:10]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)[CH2:17][C@@H:12]2[CH2:11]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[O:8][CH2:9][C@@H:10]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[N:19]=[CH:20][C:21]([F:24])=[CH:22][N:23]=3)[CH2:17][C@@H:12]2[CH2:11]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57017793HCID 57017793, compound

Product 1

HCID 70201669HCID 70201669, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.15 g (0.39 mmol) of (7S,8aS)-7-(3-(methoxycarbonyl)phenoxy)methyl-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Example 11j) in 15 mL of anhydrous ethyl ether was added dropwise to an ice-cold suspension of 0.029 g (0.78 mmol) of lithium aluminum hydride in 15 mL of anhdrous ethyl ether and the mixture stirred for 30 min. The reaction was carefully quenched at 0° C. with 0.029 mL of water, 0.029 mL of 15% sodium hydroxide, and 0.087 mL of water. The precipiate which formed was filtered through Celite, the filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 chloroform:methanol gave 0.099 g (72%) of the title compound. Mp (.HCl) 85-89° C. HRMS calc'd for C19H24FN4O2 (MH+): 359.1883, found: 359.1895.

Workup

  1. customThe reaction was carefully quenched at 0° C. with 0.029 mL of water, 0.029 mL of 15% sodium hydroxide, and 0.087 mL of water
  2. customThe precipiate which formed
  3. filtrationwas filtered through Celite
  4. concentrationthe filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 chloroform

Sources & evidence

ORD record
ord-52355a617a9344628dbd80b545116848
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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