Benzaldehyde → HCID 131718098, compound

HRID 2255544Notes

Reaction equation

HRID 2255544 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])[N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33]([C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=1)[C:5]2=[O:53].[CH:54](=O)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.[BH3-]C#N.[Na+]>CCO.C1COCC1>[CH2:54]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])[N:6]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33]([C:34]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:32]=[N:31][N:30]=3)=[CH:21][CH:22]=1)[C:5]2=[O:53])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 131718094HCID 131718094, compound

Product 1

HCID 131718098HCID 131718098, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 100 mg (0.14 mmol) of the amine from Example 40 in 2 mL of EtOH was added 16 mg (0.15 mmol) of benzaldehyde. The reaction mixture was heated to 60° C. for 1 hour, cooled to 0° C. and treated with 0.29 mL (0.29 mmol) of a 1M solution of NaCNBH3 in THF. The reaction mixture was stirred overnight, concentrated in vacuo, and the residue partitioned between 25 mL of EtOAc and 15 mL of water. The phases were separated and the organic phase was washed with brine (1×25 mL) and dried over MgSO4. The mixture was filtered and concentrated in vacuo and the residue was purified by flash chromatography over silica gel eluting with 25% EtOAc/hexanes to give 45 mg (0.06 mmol) of a yellow foam. 1H-NMR (CDCl3 300 MHz): 0.88 (t, 3H, J=7.4 Hz), 1.31 (m, 2H), 1.66 (m, 2H), 2.61 (3 line m, 2H, J=7.8 Hz), 4.32 (bs, 1H), 4.43 (bs, 2H), 5.28 (bs, 2H), 6.88 (m, 8H), 7.08 (m, 3H), 7.20-7.53 (m, 19H), 7.91 (d, 1H).

Workup

  1. temperaturecooled to 0° C.
  2. concentrationconcentrated in vacuo
  3. customthe residue partitioned between 25 mL of EtOAc and 15 mL of water
  4. customThe phases were separated
  5. washthe organic phase was washed with brine (1×25 mL)
  6. dry with materialdried over MgSO4
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by flash chromatography over silica gel eluting with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-8c5e4a5a7916439c988b40c5c0ff3e15
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

Loading…