Formaldehyde → HCID 18357303, compound

HRID 428331Notes

Reaction equation

HRID 428331 reaction equation
Cl.CO.C=O.[C:6]([BH3-])#N.[Na+].[CH:10]1([NH:14][CH2:15][CH2:16][CH:17]([C:24]2[CH:29]=[C:28]([Br:30])[CH:27]=[CH:26][C:25]=2[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12][CH2:11]1>CO>[CH:10]1([N:14]([CH3:6])[CH2:15][CH2:16][CH:17]([C:24]2[CH:29]=[C:28]([Br:30])[CH:27]=[CH:26][C:25]=2[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18357368HCID 18357368, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 18357303HCID 18357303, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 M HCl-methanol (0.46 mL, 2.32 mmol), formaldehyde (0.870 g, 28.97 mmol) and sodium cyanoborohydride (0.255 g, 4.056 mmol) were added to a solution of N-cyclobutyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropanamine (2.61 g, 5.79 mmol) in methanol (8 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was chromatographed on silica (hexane-triethylamine, 9:1). Yield 1.59 g (59%); 1H NMR (CDCl3) δ1.59 (m, 2H), 1.73 (m, 2H), 1.91 (m, 2H), 2.06 (s, 3H), 2.16 (m, 4H), 2.68 (m, 1H), 4.38 (t, 1H), 5.00 (s, 2H), 6.72 (d, IH), 7.12-7.58 (m, 12H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed on silica (hexane-triethylamine, 9:1)

Sources & evidence

ORD record
ord-660c7c22538e4bccb482b8af9f0d0a89
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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