Sodium Bicarbonate → HCID 67337045, compound

HRID 1674685Notes

Reaction equation

HRID 1674685 reaction equation
[CH2:1]([O:3][C@H:4]([CH3:41])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][NH:17][CH2:16][C@H:15]2[CH2:37][NH:38][CH:39]=O)=[CH:10][CH:9]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:3][C@H:4]([CH3:41])[CH2:5][O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][NH:17][CH2:16][C@H:15]2[CH2:37][NH:38][CH3:39])=[CH:12][CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 42633024HCID 42633024, compound

Product 1

HCID 67337045HCID 67337045, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 mmol of N-{(3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidin-3-ylmethyl}-formamide (example 7) 8 ml of THF is mixed with 2 mmol of LiAlH4 (1M in THF) and stirred at RT for 13 h (conversion checked by HPLC or TLC), then the reaction mixture is heated to 40° C. for 2 h. The reaction mixture is poured on saturated aqueous NaHCO3 solution and extracted with TBME (3×). The combined organic phases are washed with H2O and brine and evaporated in vacuo. The title compound is obtained from the residue by flash chromatography (SiO2 60F) and identified based on the Rf value.

Workup

  1. temperaturethe reaction mixture is heated to 40° C. for 2 h
  2. extractionextracted with TBME (3×)
  3. washThe combined organic phases are washed with H2O and brine
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-fef43fc464894db6a49125e38935b14d
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

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