Diisopropylethylamine → 1-Benzyl-3(SR)-(4-(N-(benzyloxycarbonyl)-N-sec-butylamino)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

HRID 1276493Notes

Reaction equation

HRID 1276493 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.Cl.[CH2:22]([O:29][C:30]([N:32]([CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH:33]([CH2:35][CH3:36])[CH3:34])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C.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:40]2[CH2:39][CH2:38][CH:37]([N:32]([C:30]([O:29][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:31])[CH:33]([CH2:35][CH3:36])[CH3:34])[CH2:42][CH2:41]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 186776854-(N-(benzyloxycarbonyl)-N-secbutylamino)piperidine-hydrochlorideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine

Product 1

HCID 541198091-Benzyl-3(SR)-(4-(N-(benzyloxycarbonyl)-N-sec-butylamino)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidineYield 80.7%

Procedure

The title compound was prepared from 20 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 24 mg of 4-(N-(benzyloxycarbonyl)-N-secbutylamino)piperidine-hydrochloride, 0.013 mL of DIEA and 24 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 32 mg of the title compound. HPLC (YMC "Octyl" 4.6×250 mm column, 60:40 v/v H2O/CH3CN+0.5% TFA, 1.5 mL/min, 200 nm): Retention Time: 12.99 min. 1H NMR (300 MHz, CDCl3): δ0.70-0.82 (m, 3H), 1.16 (t, J =6.4 Hz, 3H), 1.37-1.95 (m, 10H), 2.34-2.66 (m, 6H), 2.83-2.99 (m, 4H), 3.69 (ABq, J =13 Hz, 2H), 5.11 (s, 2H), 7.14-7.39 (m, 15H). Mass Spectrum (ESI): 540.6 (M+H).

Sources & evidence

ORD record
ord-846e8d5eca4b4ff5942f15ba0a81c1b6
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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