Aluminium lithium hydride → HCID 70198729, compound

HRID 1594581Notes

Reaction equation

HRID 1594581 reaction equation
C[O:2][C:3]([CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:3][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70197760HCID 70197760, compound

Product 1

HCID 70198729HCID 70198729, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.15 g (0.33 mmol) of (7S,8aS)-7-(4-((methoxycarbonyl)methyl)phenoxy)methyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Example 13d) in 15 mL of anhydrous ethyl ether was added dropwise to an ice-cold suspension of 0.027 g (0.65 mmol) of lithium aluminum hydride in 15 mL of anhdrous ethyl ether and the mixture stirred for 30 minutes. The reaction was carefully quenched at 0° C. with 0.027 mL of water, 0.027 mL of 15% sodium hydroxide, and 0.081 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 0.13 g (95%) of the title compound. Mp (.HCl) 199-202° C. HRMS calc'd for C21H27ClN3O2 (MH+): 388.1792, found: 388.1807.

Workup

  1. customThe reaction was carefully quenched at 0° C. with 0.027 mL of water, 0.027 mL of 15% sodium hydroxide, and 0.081 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-74442e17581647209a216ac33c6a9e2b
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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