Aluminium lithium hydride → HCID 70200310, compound

HRID 861353Notes

Reaction equation

HRID 861353 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[N:25]=[CH:24][C:23]([F: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: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[N:21]=[CH:22][C:23]([F:26])=[CH:24][N:25]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57016126HCID 57016126, compound

Product 1

HCID 70200310HCID 70200310, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.13 g (0.33 mmol) of (7S,8aS)-7-(4-((methoxycarbonyl)methyl)phenoxy)methyl-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Example 11i) in 15 mL of anhydrous ethyl ether was added dropwise to an ice-cold suspension of 0.025 g (0.65 mmol) of lithium aluminum hydride in 15 mL of anhydrous ethyl ether and the mixture stirred for 30 min. The reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 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 ethyl acetate:methanol gave 0.075 g (63%) of the title compound. mp (.HCl) 145°-147° C. HRMS calcd for C20H26FN4 O2 (MH+): 373.2040, found: 373.2054.

Workup

  1. customThe reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 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 ethyl acetate

Sources & evidence

ORD record
ord-12b82b0127504299966061e250f6691f
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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