Cyclopropanecarboxaldehyde → HCID 58938011, compound

HRID 1182047Notes

Reaction equation

HRID 1182047 reaction equation
[CH3:1][CH:2]([CH3:25])[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[O:16][C:15]3[CH:17]=[CH:18][C:19]([C:21]([NH2:23])=[O:22])=[CH:20][C:14]=3[CH2:13][CH2:12][C:11]=2[CH:24]=1.[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1.[BH3-]C#N.[Na+]>CO.CC(O)=O>[CH:26]1([CH2:29][N:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[O:16][C:15]4[CH:17]=[CH:18][C:19]([C:21]([NH2:23])=[O:22])=[CH:20][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:4][CH2:3][CH:2]([CH3:25])[CH3:1])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11427733HCID 11427733, compound

Product 1

HCID 58938011HCID 58938011, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of amine of example 1 (30 mg, 0.09 mmol) in MeOH-AcOH 5% (0.5 mL) add cyclopropanecarboxaldehyde (0.18 mmol). Stir the mixture at room temperature overnight. Add NaBH3CN and stir the mixture at room temperature for about two hours. Add more aldehyde (1.5 mmol) and stir overnight. Purify by SCX ion-exchange chromatography to obtain the title compound (22 mg). 1H-NMR (CD3OD, 300 MHz): 7.72-7.69 (m, 2H), 7.21-7.09 (m, 4H), 3.64 (s, 2H), 3.14 (bs, 4H), 2.61-2.56 (m, 2H), 2.37 (d, 2H, J=6.5 Hz), 1.60-1.37 (m, 4H), 0.87 (d, 6H, J=6.7 Hz), 0.55-0.49 (m, 2H), 0.13-0.08 (m, 2H). Electrospray MS M+1 ion=393.

Workup

  1. stirringstir overnight
  2. customPurify by SCX ion-exchange chromatography

Sources & evidence

ORD record
ord-3a6dc22313e74611ba9b454dbc2d0b30
Source dataset
uspto-grants-2007_10
Patent number
US07288543B2

Reaction notes

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