2-Naphthalenecarboxaldehyde → HCID 59773010, compound

HRID 2220687Notes

Reaction equation

HRID 2220687 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13][NH2:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH:25]=O.[Na]>ClCCl>[CH:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13][NH:14][CH2:25][C:16]2[CH:17]=[CH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 5360545SodiumHCID 51898061HCID 51898061, compound

Product 1

HCID 59773010HCID 59773010, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—C-(1-Cyclohexylmethyl-pyrrolidin-2-yl)-methylamine (prepared according to scheme 2) 0.24 g (1 mmol), and naphthalene-2-carbaldehyde 0.19 g (1.2 mmol), were dissolved in 10 mL dichloromethane. To this mixture was added sodium triacethoxyborohydride 0.51 g (2 mmol), and molecular sieve. The reaction was stirred overnight under nitrogen. Molecular sieve was filtered, washed with 3 mL HCl, acidic layer was transformed to basic pH, with powder sodium bicarbonate, and extracted with ethyl acetate. The combined organic layer dried over magnesium sulfate, filtered and concentrated, yield to 100 mg of yellow oil.

Workup

  1. filtrationMolecular sieve was filtered
  2. washwashed with 3 mL HCl, acidic layer
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6c40303831c428a9a0585b99f411aaa
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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