Cyclopentanecarbaldehyde → HCID 61344637, compound

HRID 2043917Notes

Reaction equation

HRID 2043917 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC1C=C(C=CC=1F)N.C1(C=O)CCCC1.[BH3-]C#N.[Na+]>C1COCC1.CO>[CH:1]1([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 70106CyclopentanecarbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66960773HCID 66960773, compound

Product 1

HCID 61344637HCID 61344637, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Preparation of cyclopentylmethyl-(3,4-difluoro-phenyl)-amine-3,4-Difluoroaniline (18.5 mmol) dissolved in 50 ml of THF:MeOH (1:1) was added cyclopentanecarbaldehyde (20.4 mmol) and 3 Å molsieves (5 g) and stirred for 0.5 h at RT. Then NaBH3CN (37.1 mmol=2 eqv.) was added and the reaction mixture was stirred for 13H at room temperature before it was filtered and the filtrate was concentrated in vacuo to give crude cyclopentylmethyl-(3,4-difluorophenyl)-amine.

Workup

  1. stirringthe reaction mixture was stirred for 13H at room temperature before it
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-38f1003bbc5240bd8ab919f0b814f544
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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