Dimethylamine → HCID 15871737, compound

HRID 1738906Notes

Reaction equation

HRID 1738906 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]([CH2:15][C:16]([CH:19]=O)([CH3:18])[CH3:17])[C:13](=[O:21])[C@@H:12]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:11][C@H:10]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)[C:9]=2[CH:38]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(O)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]([CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19][N:2]([CH3:3])[CH3:1])[C:13](=[O:21])[C@@H:12]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:11][C@H:10]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)[C:9]=2[CH:38]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 15871736HCID 15871736, compound

Product 1

HCID 15871737HCID 15871737, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

Dimethylamine (0.18 g, 4.0 mmol) was added to ethyl trans-7-chloro-5-(1-naphthyl)-1-(2-formyl-2-methylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1 -benzoxazepine-3-acetate (2.0 g, 4.05 mmol) in titanium tetraisopropoxide (3.45 g, 12.15 mmol) at room temperature. Stirring for 1h was followed by addition of sodium cyanoborohydride (0.38 g, 6.0 mmol) and ethanol (20 ml). The mixture was stirred for another 18 hours before 2 N sodium hydroxide was added. The mixture was extracted several times with dichloromethane, and the combined organic layers were dried with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (dichloromethane/ methanol/aqueous ammonia 99:1:0.1 to 98:2:0.2) to give the title compound (1.23 g, 58%) as a yellow oil.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted several times with dichloromethane
  3. dry with materialthe combined organic layers were dried with MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography (dichloromethane/ methanol/aqueous ammonia 99:1:0.1 to 98:2:0.2)

Sources & evidence

ORD record
ord-342b6ad0ec4443c29f81c9212403d8d0
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

Loading…