4-Fluorobenzaldehyde → N-[3-[1-(4-fluoro-benzyl)-piperidin-4-yl]-5-isopropoxy-6-methyl-isochroman-1-ylmethyl]-formamide

HRID 2074420Notes

Reaction equation

HRID 2074420 reaction equation
[CH:1]([O:4][C:5]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][C@@H:8]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[O:9][C@H:10]2[CH2:16][NH:17][CH:18]=[O:19])([CH3:3])[CH3:2].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:23]2[CH2:22][CH2:21][CH:20]([CH:8]3[CH2:7][C:6]4[C:11](=[CH:12][CH:13]=[C:14]([CH3:15])[C:5]=4[O:4][CH:1]([CH3:3])[CH3:2])[CH:10]([CH2:16][NH:17][CH:18]=[O:19])[O:9]3)[CH2:25][CH2:24]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11638795N-((1R,3S)-5-Isopropoxy-6-methyl-3-(4-piperidinyl)-1-isochromanylmethyl)formamide

Product 1

HCID 86612289N-[3-[1-(4-fluoro-benzyl)-piperidin-4-yl]-5-isopropoxy-6-methyl-isochroman-1-ylmethyl]-formamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a suspension of N-((1R,3S)-5-Isopropoxy-6-methyl-3-(4-piperidinyl)-1-isochromanylmethyl)formamide (1.0 mmol) with 4-fluorobenzaldehyde (3.0 mmol) and sodium triacetoxyborohydride (3.0 mmol) in dichloromethane (5 mL) at room temperature overnight. Apply the reaction mixture directly to a 5 g SCX column and elute and concentrate the appropriate fractions to obtain N-[3-[1-(4-fluoro-benzyl)-piperidin-4-yl]-5-isopropoxy-6-methyl-isochroman-1-ylmethyl]-formamide. Use the compound directly for the next step.

Workup

  1. washApply the reaction mixture directly to a 5 g SCX column and elute
  2. concentrationconcentrate the appropriate fractions

Sources & evidence

ORD record
ord-bcf55261ce03457fb7e3ed6e4bd08e9f
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

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