Tetrahydrofuran → HCID 66734434, compound

HRID 1929717Notes

Reaction equation

HRID 1929717 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:19][CH3:20])=[N:15][C:16]([CH:17]=[O:18])=[C:10]2[CH:9]1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.C1COCC1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:19][CH3:20])=[N:15][C:16]([CH2:17][OH:18])=[C:10]2[CH:9]1[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:27][CH:28]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 86640827HCID 86640827, compound

Product 1

HCID 66734434HCID 66734434, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) colorless solution of 3-ethyl-1-formyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (19.9 mg; 0.044 mmol) in anhydrous toluene (2 ml) was added dropwise 1M DIBAL in THF (88 μl; 2 eq.). The resulting yellow homogeneous solution was further stirred at −78° C. for 10 min., and then at rt for 1 h. The resulting crude mixture was purified by preparative HPLC to give the pure product 3-ethyl-1-hydroxymethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (16 mg; 0.035 mmol; 80%). LC-MS: tR=0.91 min.; [M+H]+=454.27 g/mol.

Workup

  1. waitat rt for 1 h
  2. customThe resulting crude mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-d340ab67e4004324a094f0782961df51
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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