2-Naphthalenecarboxaldehyde → HCID 59717695, compound

HRID 2224645Notes

Reaction equation

HRID 2224645 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[CH2:13]([N:20]1[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+]>CO.O>[CH2:13]([N:20]1[CH2:24][CH2:23][C@H:22]([NH:25][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 4311764Sodium borohydride

Product 1

HCID 59717695HCID 59717695, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-naphthaldehyde (2.0 g, 12.8 mmol) and (3S)-1-benzyl-3-amino-pyrrolidine (2.37 g, 13.4 mmol) in methanol (30 mL) was stirred under nitrogen at room temperature for 6 hours. Sodium borohydride (969 mg, 25.6 mmol) was added and the reaction mixture left at room temperature for 18 hours. The reaction mixture was diluted with water and extracted into ethyl acetate (×3) and the organics were combined, dried over magnesium sulphate, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with dichloromethane:methanol 100:0 to 97:3 to yield the title product, 4.01 g.

Workup

  1. extractionextracted into ethyl acetate (×3)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel eluting with dichloromethane:methanol 100:0 to 97:3

Sources & evidence

ORD record
ord-e3f0429509bc4b9aab06e740aa9618b7
Source dataset
uspto-grants-2008_05
Patent number
US07378436B2

Reaction notes

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