Ethyl 4-piperidinecarboxylate → HCID 70200252, compound

HRID 1276499Notes

Reaction equation

HRID 1276499 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.[NH:21]1[CH2:31][CH2:30][CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:22]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:21]2[CH2:22][CH2:23][CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:30][CH2:31]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 221160811-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine

Product 1

HCID 70200252HCID 70200252, compound

Procedure

The title compound was prepared from 400 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 0.24 mL of ethyl isonipecotate and 480 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 363 mg of the title compound. RF : 0.31 (50% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3): δ1.22 (t, J=7.1 Hz, 3H), 1.54-1.89 (m, 6H), 2.13-2.21 (m, 1H ), 2.33-2.64 (m, 6H), 2.77-2.97 (m, 4H), 3.65 (ABq, J=13 Hz, 2H), 4.09 (q, J=7.1 Hz, 2H), 7.14-7.37 (m, 10H). Mass Spectrum (CI): 407.3 (M+H).

Sources & evidence

ORD record
ord-7457a28b569345579c7531d8e3f441ea
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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