Pyrrolidine → HCID 24801218, compound

HRID 386457Notes

Reaction equation

HRID 386457 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([C:19]3[O:20][C:21]([C:24]4[N:29]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:26][CH:25]=4)=[CH:22][N:23]=3)=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[N:34]1([CH2:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([C:19]4[O:20][C:21]([C:24]5[N:29]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:26][CH:25]=5)=[CH:22][N:23]=4)=[O:18])=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86645815HCID 86645815, compound

Product 1

HCID 24801218HCID 24801218, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Methyl 6-(2-(3-(4′-formylbiphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate (19 mg, 0.043 mmol) and pyrrolidine (0.005 mL, 0.07 mmol) were dissolved in dichloroethane (2 mL) and NaBH(OAc)3 (18 mg, 0.086 mmol) was added. The reaction solution was stirred under an atmosphere of Ar at ambient temperature for 3 h and then quenched with saturated aqueous NaHCO3. The crude product was extracted with EtOAc and the solvent was removed in vacuo. The crude product was purified by flash chromatography (SiO2, 2.5% Et3N/EtOAc) to furnish methyl 6-(2-(3-(4′-(pyrrolidin-1-ylmethyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate as a cloudy oil (16 mg, 75%): 1H NMR (CDCl3, 600 MHz) δ 8.11 (d, 1H, J=7.7 Hz), 8.02 (d, 2H, J=9.0 Hz), 7.96 (t, 1H, J=7.8 Hz), 7.53-7.51 (m, 4H), 7.38 (d, 2H, J=8.0 Hz), 7.33 (d, 2H, J=8.0 Hz), 4.03 (s, 3H), 3.65 (s, 2H), 3.51 (t, 2H, J=7.6 Hz), 3.15 (t, 2H, J=7.6 Hz), 2.54 (s, 4H), 1.81-1.79 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 187.3, 165.1, 157.4, 152.4, 148.5, 146.5, 139.5, 139.2, 139.1, 138.3, 138.3, 129.3, 128.8, 128.0, 127.1, 126.8, 125.2, 123.3, 60.4, 54.2, 53.1, 40.6, 29.3, 23.4; HR ESI-TOF m/z 496.2233 (M+H+, C30H29N3O4, requires 496.2231).

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionThe crude product was extracted with EtOAc
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography (SiO2, 2.5% Et3N/EtOAc)

Sources & evidence

ORD record
ord-3b97a2ffc1e049c29e49eb4084616f99
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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