Sodium cyanoborohydride → HCID 18665737, compound

HRID 399139Notes

Reaction equation

HRID 399139 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH:15]=O)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.C([C:27]1[CH:41]=[CH:40][C:30]([CH2:31][N:32]2[C:36]([CH2:37][CH2:38][NH2:39])=[CH:35][N:34]=[CH:33]2)=[CH:29][CH:28]=1)#N.[BH3-][C:43]#[N:44].[Na+]>CO>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([CH2:15][NH:39][CH2:38][CH2:37][C:36]3[N:32]([CH:31]([C:43]#[N:44])[C:30]4[CH:29]=[CH:28][CH:27]=[CH:41][CH:40]=4)[CH:33]=[N:34][CH:35]=3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 18665738HCID 18665738, compoundHCID 70193148HCID 70193148, compound

Product 1

HCID 18665737HCID 18665737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2,2-Diphenylethyl)-3(S)-piperidine carboxaldehyde (0.575 g, 1.96 mmol),3-(4-cyanobenzyl) histamine dihydrochloride (0.388 g, 1.30 mmol), and NaCNBH3 (0.123 g, 1.96 mmol) were dissolved in MeOH (15 mL) and stirred at ambient temperature overnight. The solution was concentrated and the residue taken up in EtOAc, washed with sat. NaHCO3 solution, H2O, and brine. The organics were dried, concentrated, and chromatographed (0-4% MeOH/CH2Cl2 /NH4OH) to give the title compound which was isolated as a tris HCl salt. 1H NMR (CD3OD); δ9.05 (s, 1H), 7.81 (d, 2H, J=8 Hz), 7.68 (s, 1H), 7.54 (d, 2H, J=8 Hz), 7.49-7.25 (m, 10H), 5.67 (s, 2H), 4.76-7.74 (m, 1H), 4.05-3.88 (m, 3H), 3.54-3.47 (m, 1H), 3.33-3.30 (m, 1H), 3.19-3.15 (m, 2H), 3.02-3.00 (m, 2H), 2.92-2.90 (m, 2H), 2.42 (br s, 1H), 1.99-1.91 (m, 2H), 1.82-1.78 (m, 1H), 1.31-1.28 (m, 2H).

Workup

  1. concentrationThe solution was concentrated
  2. washwashed with sat. NaHCO3 solution, H2O, and brine
  3. customThe organics were dried
  4. concentrationconcentrated
  5. customchromatographed (0-4% MeOH/CH2Cl2 /NH4OH)

Sources & evidence

ORD record
ord-c72c55c2912c4c4db1308b3ba62b48d4
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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