Sodium Bicarbonate → HCID 86596766, compound

HRID 1816071Notes

Reaction equation

HRID 1816071 reaction equation
Cl[C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][CH2:24][CH2:25][OH:26])=[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].[CH3:27][N:28]([CH2:36][CH:37]=O)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].[C:39](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[OH:26][CH2:25][CH2:24][N:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:2]([CH3:39])=[C:3]([C:4]([NH:6][CH2:7][C:8]23[CH2:15][CH:14]4[CH2:16][CH:10]([CH2:11][CH:12]([CH2:13]4)[CH2:17]2)[CH2:9]3)=[O:5])[CH:18]=1)[CH2:37][CH2:36][N:28]([CH3:27])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 21900026HCID 21900026, compound

Product 1

HCID 86596766HCID 86596766, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-[[(2-hydroxyethyl)amino]methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.30 g, Example 71c), methyl(2-oxoethyl)-carbamic acid, 1,1-dimethylethyl ester (0.276 g), sodium triacetoxyborohydride (0.720 g) and dichloromethane (50 ml) were stirred together under nitrogen for 24 h. The mixture was poured into saturated aqueous sodium hydrogencarbonate solution, extracted into dichloromethane, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified on silica (eluting with 19:1 dichloromethane/methanol) to afford the subtitled compound (0.285 g).

Workup

  1. extractionextracted into dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified on silica (eluting with 19:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-aea7d5996b4d4eebb66ee3adabf47ca5
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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