Aluminum(III) Chloride → HCID 67090221, compound

HRID 2074422Notes

Reaction equation

HRID 2074422 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH:11]([O:14][C:15]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][C@@H:18]([CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:32][CH2:31]1)[O:19][C@H:20]2[CH2:26][NH:27][CH:28]=O)([CH3:13])[CH3:12]>C1COCC1>[CH:11]([O:14][C:15]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][C@@H:18]([CH:30]1[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:34][CH2:35]1)[O:19][C@H:20]2[CH2:26][NH:27][CH3:28])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 86612291HCID 86612291, compound

Product 1

HCID 67090221HCID 67090221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 0.5M LiAlH4 in THF (3 mL) at 8° C., add of AlCl3 (35 mg) and (1R,3S)-N-[5-Isopropoxy-6-methyl-3-(1-phenethyl-piperidin-4-yl)-isochroman-1-ylmethyl]-formamide in THF (2 mL). Allow the reaction mixture to warm to 20° C. and stir for 4 hours. Cool to 8° C. and quench by slow addition of saturated, aqueous. NH4Cl to pH 8. Add EtOAc (8 mL) and then filter the mixture separate the organic layer and concentrate. Purify the residue by chromatography on a 1 g silica gel column (eluent: 10% CH3OH/CH2Cl2). Collect the appropriate fractions and concentrate to obtain the title compound.

Workup

  1. temperatureCool to 8° C.
  2. customquench by slow addition of saturated, aqueous
  3. filtrationAdd EtOAc (8 mL) and then filter the mixture
  4. customseparate the organic layer
  5. concentrationconcentrate
  6. customPurify the residue by chromatography on a 1 g silica gel column (eluent: 10% CH3OH/CH2Cl2)
  7. customCollect the appropriate fractions
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-c879d7c187304fbeba81a306f30b8158
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

Loading…