Methyl Benzoate → HCID 131733077, compound

HRID 924318Notes

Reaction equation

HRID 924318 reaction equation
[H-].[Na+].[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]2[N:14]([CH2:15]C3C=CC(OC)=CC=3)C(=O)C[CH2:11]2)=[CH:5][CH:4]=1.CO[C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[NH4+:41].[Cl-].C([O:46][CH2:47][CH3:48])(=O)C>C1(C)C=CC=CC=1>[C:33]([C@H:48]1[CH2:11][CH:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:8][CH:7]=2)[N:14]([CH2:15][N:41]2[CH2:5][CH2:4][CH2:3][CH2:8]2)[C:47]1=[O:46])(=[O:40])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 7150Methyl BenzoateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 53311905HCID 53311905, compound

Product 1

HCID 131733077HCID 131733077, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of sodium hydride (150 mg, 55% in mineral oil, 3.75 mmol) in toluene (1 mL) is added (5S)-biphenyl-4-ylmethyl-1-(4-methoxybenzyl)pyrrolidin-2-one (3a, R1=p-methoxybenzyl) (694 mg, 1.86 mmol) followed by addition of benzoic acid methyl ester (253 mg, 1.86 mmol), the resulting mixture is then heated at 130° C. for 9 h. After cooling to room temperature, NH4Cl (sat. aq, 5 mL) is added followed by ethyl acetate (3 mL). The organic layer is separated, washed with brine and concentrated to give (3R/S)-benzoyl-(5S)-biphenyl-4-ylmethyl-1-(4-methoxybenzyl)pyrrolidin-2-one (4a, R1=p-methoxybenzyl, R4=phenyl) as a mixture of (3S,5R) and (3R,5R) diastereomers (50:40 as determined by HPLC). 1HNMR (400 MHz, DMSO): 1.82-2.08 (m, 2H), 2.25-2.70 (m, 2H), 3.00-3.26 (m, 2H), 3.73 (s, 3H), 4.00-4.10 (m, 1H), 4.20-4.52 (m, 1H), 4.94-5.09 (m, 1H), 6.86˜8.10 (18H, m, aromatic). MS (ESI, m/e) 476 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer is separated
  3. washwashed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0e14330477de484aacfb3fda85e4519b
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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