(2R)-2-(Methoxymethyl)pyrrolidine → HCID 57959861, compound

HRID 1698513Notes

Reaction equation

HRID 1698513 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH:8]=O)=[O:5].[CH3:27][O:28][CH2:29][C@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH:7]([C:10]1[CH:11]=[CH:12][C:13]([S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[CH:14][CH:15]=1)[CH2:8][N:31]1[CH2:32][CH2:33][CH2:34][C@@H:30]1[CH2:29][O:28][CH3:27])=[O:5]

Participants

5

Reactant 3

HCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635962HCID 86635962, compound

Product 1

HCID 57959861HCID 57959861, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2,4-dichloro-N-{2-oxo-1-[4-(propylsulphonyl)phenyl]-ethyl}benzamide (135 mg, 0.33 mmol) in 1,2-dichloroethane (5 mL) under nitrogen was added (R)-2-(methoxymethyl)pyrrolidine (81 □L, 0.66 mmol) followed by sodium triacetoxyborohydride (138 mg, 0.65 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of satd. NaHCO3(aq) and the product extracted into ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. One diastereoisomer of the title compound was isolated in pure form following preparative HPLC. 1H NMR δ (400 MHz, CDCl3) δ 1.00 (3H, t, J=7.4 Hz), 1.32-1.40 (1H, m), 1.52-1.59 (2H, m), 1.71-1.82 (4H, m), 1.96-2.04 (1H, m), 2.37-2.42 (1H, m), 2.87 (1H, br s), 3.00 (3H, s), 3.03-3.07 (2H, m), 3.21-3.35 (3H, m), 5.15-5.19 (1H, m), 7.34 (1H, dd, J=1.9, 8.3 Hz), 7.47 (1H, d, J=1.9 Hz), 7.59-7.61 (3H, m), 7.87 (2H, d, J=8.3 Hz), 8.31 (1H, d, J=5.3 Hz); m/z (ES+) 515 (M+H), 513 (M+H).

Workup

  1. customThe reaction mixture was quenched by addition of satd
  2. extractionNaHCO3(aq) and the product extracted into ethyl acetate (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6e48e0c3beb4fc4b9c725fd5837bad9
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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