Borane → (R)-N-(4-methoxy-3-(morpholinosulfonyl)benzyl)-1-(3-chlorophenyl)ethanamine

HRID 1801582Notes

Reaction equation

HRID 1801582 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([S:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:13]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.B>C1COCC1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][NH:10][C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH3:9])=[CH:13][C:14]=1[S:20]([N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 6331BoraneHCID 26908119(R)-N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide

Product 1

HCID 24953407(R)-N-(4-methoxy-3-(morpholinosulfonyl)benzyl)-1-(3-chlorophenyl)ethanamineYield 18.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)—N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide 43 (0.948 g, 2.16 mmol) in THF (9 mL) at room temperature was added borane (0.124 g, 8.96 mmol) (9 mL, 1 M in THF). The reaction mixture was heated to reflux for 24 h, quenched with 1 M NaOH, and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes) gave (R)—N-(4-methoxy-3-(morpholinosulfonyl)benzyl)-1-(3-chlorophenyl)ethanamine 44 (0.166 g, 18.1% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.35 (d, J=6.5 Hz, 3H), 3.21-3.24 (m, 4H), 3.55-3.63 (m, 2H), 3.71-3.78 (m, 4H), 3.91 (s, 3H), 6.97 (d, J=8.6 Hz, 1H), 7.20-7.29 (m, 3H), 7.33 (s, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.78 (s, 1H). Mass spectrum: calculated for C20H25ClN2O4S 424.1. found 425.2 (M++1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. customquenched with 1 M NaOH
  4. additiondiluted with EtOAc
  5. washThe organic phase was washed with water (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0a698f7246324e3b82c336884eeab795
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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