Dichloromethane → N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

HRID 1794705Notes

Reaction equation

HRID 1794705 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:34])[CH2:18][N:19]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][C:12]=1[NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)Cl>CO.C1COCC1>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:34])[CH2:18][N:19]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][C:12]=1[NH:35][S:36]([CH3:39])(=[O:37])=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 22220380N-[2-Benzyloxy-5-(2-dibenzylamino-1-oxo-ethyl)-phenyl]-methanesulfonamide

Product 1

HCID 22220247N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Sodium borohydride (0.37 g, 9.7 mmol) was added in portions to a stirred solution of N-[2-benzyloxy-5-(2-dibenzylamino-1oxo-ethyl)-phenyl]-methanesulfonamide (1.0 g, 1.9 mmol) (which was obtained in Example 6) in 20 mL of methanol/THF (5:2) at room temperature and the resulting solution was stirred for 2 hours. Methylene chloride was added and the resulting solution was washed with aqueous sodium bicarbonate, dried over MgSO4 and the solvents were removed. Recrystallization from methylene chloride/hexanes gave the title compound as a crystalline solid; 1H NMR (300 MHz, CDCl3) δ 2.58 (d, J=6.7 Hz, 2 H), 2.86 (s, 2 H), 2.92 (s, 2 H), 3.55 (d, J=13.5 Hz, 2 H), 3.70 (d, J=13.5 Hz, 2 H), 4.11 (s, 1 H), 4.64 (t, J=6.7 Hz, 1 H), 5.10 (s, 2 H), 6.92 (d, J=8.5 Hz, 1 H), 7.00 (dd, J=8.5, 2.0 Hz, 1 H), 7.20–7.50 (m, 16 H), 7.89 (brs, 1 H); MS (ES) m/z: 517.1 (MH+); HRMS Calcd. for C30H32N2O4S(M+): 516.2083. Found: 516.2074.

Workup

  1. washthe resulting solution was washed with aqueous sodium bicarbonate
  2. dry with materialdried over MgSO4
  3. customthe solvents were removed
  4. customRecrystallization from methylene chloride/hexanes

Sources & evidence

ORD record
ord-3a37297f98a34760a35f8458eb092ab1
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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