Diisopropylethylamine → HCID 70273689, compound

HRID 1276497Notes

Reaction equation

HRID 1276497 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.C1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[CH2:37]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[CH2:41][CH2:40][NH:39][CH2:38]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:39]2[CH2:38][CH2:37][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[CH2:41][CH2:40]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidineHCID 88247005HCID 88247005, compound

Product 1

HCID 70273689HCID 70273689, compoundYield 49.1%

Procedure

The title compound was prepared from 20 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 28 mg of 2, 3, 4, 5-tetrahydro-1H-benzo[d]-azepine-picrate salt, 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 14.5 mg of the title compound. RF : 0.53 (50% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3): δ2.42-3.02 (m, 16H), 3.67 (ABq, J=13 Hz, 2H), 7.00-7.38 (m, 14H). Mass Spectrum (ESI): 397.1 (M+H).

Sources & evidence

ORD record
ord-64522e09464d4d59a3902b0a2ab54478
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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