4-Phenylazepane → HCID 54191975, compound

HRID 1276498Notes

Reaction equation

HRID 1276498 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH:19]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH:27]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:30]2[CH2:31][CH2:32][CH2:33][CH:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 4362104-PhenylazepaneHCID 5049666Sodium triacetoxyborohydrideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine

Product 1

HCID 54191975HCID 54191975, compoundYield 58.7%

Procedure

The title compound was prepared from 20 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 13 mg of 4-phenyl-perhydro-azepine and 25 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 18.5 mg of the title compound. RF : 0.37 (50% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3): δ1.48-1.83 (m, 6H), 2.37-2.69 (m, 10H), 2.88-3.01 (m, 3H), 3.67 (ABq, J=13 Hz, 2H), 7.09-7.39 (m, 15H). Mass Spectrum (CI): 425.3 (M+H).

Sources & evidence

ORD record
ord-0d180e48ae16482c82040b43016255f4
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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