Acetaldehyde → HCID 21071635, compound

HRID 1371934Notes

Reaction equation

HRID 1371934 reaction equation
[CH:1](=O)[CH3:2].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:33].[Na+].O.C(#N)C>ClCCl.C(O)(=O)C.CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:32][CH3:33])[CH:10]=[C:9]2[CH2:15][CH2:16][N:17]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)[CH2:1][CH3:2]

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18373917Acetonitrile--water (1/1)HCID 21071637HCID 21071637, compound

Product 1

HCID 21071635HCID 21071635, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Add acetaldehyde (0.080 mL; 0.77 mmol) to a solution of N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-3-phenyoxybenzylamine (free base, 55.5 mg, 0.149 mmol) in dichloromethane (1 mL) followed by a suspension of sodium triacetoxyborohydride (64 mg; 0.30 mmol) in dichloromethane (1 mL). After 44 hours, quench by the addition of methanol (0.5 mL) and concentrate in a stream of nitrogen to give a residue. Dissolve the residue in 4 mL of 5% acetic acid in methanol and partially purify by passage through a 1 gm SCX column, eluting with 1 M ammonia in methanol to give a residue. Chromatograph the residue by preparative HPLC (C-18 column, flow rate of 20 ml/min, 5–90% water/acetonitrile over 12 min) to give the title compound: MS (ES+): m/e (M+1); HPLC: (10–90% water/acetonitrile over 10 min, Tr=5.25 min).

Workup

  1. customquench by the addition of methanol (0.5 mL)
  2. concentrationconcentrate in a stream of nitrogen
  3. customto give a residue
  4. custompartially purify by passage through a 1 gm SCX column
  5. washeluting with 1 M ammonia in methanol
  6. customto give a residue

Sources & evidence

ORD record
ord-025918f218b4405aa6e8db930d6ddc94
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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