Cyclobutylamine → HCID 18357368, compound

HRID 428330Notes

Reaction equation

HRID 428330 reaction equation
Cl.CO.[CH:4]1([NH2:8])[CH2:7][CH2:6][CH2:5]1.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[CH:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:25][CH:26]=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([BH3-])#N.[Na+]>CO>[CH:4]1([NH:8][CH2:26][CH2:25][CH:24]([C:18]2[CH:19]=[C:20]([Br:23])[CH:21]=[CH:22][C:17]=2[O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 75645CyclobutylamineHCID 5003444Sodium cyanoborohydrideHCID 18357288HCID 18357288, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 18357368HCID 18357368, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 M HCl-methanol (3.50 mL, 17.71 mmol) was added to a solution of cyclobutylamine (4.50 mL, 53.15 mmol) in methanol (14 mL). The mixture was added to 3-(2-benzyloxy-5-bromophenyl)-3-phenylpropanal (Example 20.1), (3.50 g, 8.86 mmol), followed by sodium cyanoborohydride (0.389 g, 6.20 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 92:4:4). Yield 2.61 g (65%); 1H NMR (CDCl3) δ1.57 (m, 5H), 2.14 (m, 4H), 2.47 (t, 2H), 3.16 (m, 1H), 4.45 (t, 1H), 5.00 (s, 2H), 6.75 (d, 1H), 7.10-7.47 (m, 12H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 92:4:4)

Sources & evidence

ORD record
ord-a48d961c5d534357b25d4ab73fc53d6f
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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