1-Propanol, 3-amino-2,2-dimethyl- → 2-Chloro-5-[(3-hydroxy-2,2-dimethylpropylamino)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1593806Notes

Reaction equation

HRID 1593806 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:24][CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:24][CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

5

Reactant 3

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 5049666Sodium triacetoxyborohydrideHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 102955522-Chloro-5-[(3-hydroxy-2,2-dimethylpropylamino)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideYield 18.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared according to the method described in Example 2 from 2-chloro-5-formyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.150 g, Example 1b), 3-amino-2,2-dimethylpropanol (0.093 g) and sodium triacetoxyborohydride (0.134 g) in 1,2-dichloroethane (6 ml). After work-up, the resiude was purified by NPHPLC eluting with a gradient of 0-10% ethanol in dichloromethane to give the title compound as a white powder (0.035 g).

Workup

  1. customPrepared
  2. customAfter work-up, the resiude was purified by NPHPLC
  3. washeluting with a gradient of 0-10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-c1ddf8a41c444811a5c8ea7fdfc36337
Source dataset
uspto-grants-2007_11
Patent number
US07297818B2

Reaction notes

Loading…