Dimethylformamide → HCID 86631460, compound

HRID 660028Notes

Reaction equation

HRID 660028 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](C=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CN([CH:39]=[O:40])C>C(Cl)(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH2:23][CH:24]([CH2:27][CH2:28][CH2:29][CH2:30][N:1]2[C:9]3[C:4](=[C:5]([CH:39]=[O:40])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:25][CH2:26]1)=[O:20])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 589040Indole-5-carboxaldehydeHCID 27846694-(4-Methanesulfonyloxy-butyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86631460HCID 86631460, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 0° C. solution of 1H-indole-5-carbaldehyde (0.43 g, 2.96 mmol) in DMF (10 mL) was added NaH (60% in mineral oil; 0.14 mg, 3.55 mmol). After 45 min at 0° C., a solution of 4-(4-methanesulfonyloxy-butyl)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 3.15 mmol) in DMF (5 mL) was added dropwise. The mixture was warmed to rt and stirred for 18 h. The mixture was diluted with CHCl3 (20 mL) and washed with water (15 mL). The organic layer was dried and concentrated to obtain the crude residue, which was used purified by FCC to give 0.96 g (88%). MS: mass calcd. for C22H30N2O3, 370.23; m/z found, 371.4 [M+H]+.

Workup

  1. washwashed with water (15 mL)
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-955e79c016a3447fb3e350f9e5302160
Source dataset
uspto-grants-2011_12
Patent number
US08084466B2

Reaction notes

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