Acetaldehyde → 2-acetamido-N-tert-butyl-2-(2-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-3-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide

HRID 579537Notes

Reaction equation

HRID 579537 reaction equation
[CH:1](=O)[CH3:2].[C:4]([NH:7][C:8]([CH2:29][CH2:30][CH:31]1[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][NH:32]1)([CH2:16][CH2:17][CH2:18][CH2:19][B:20]1[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]1)[C:9]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:6])[CH3:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:4]([NH:7][C:8]([CH2:29][CH2:30][CH:31]1[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][N:32]1[CH2:1][CH3:2])([CH2:16][CH2:17][CH2:18][CH2:19][B:20]1[O:21][C:22]([CH3:27])([CH3:28])[C:23]([CH3:25])([CH3:26])[O:24]1)[C:9]([NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 668337032-acetamido-N-tert-butyl-2-(2-(1,2,3,4-tetrahydroisoquinolin-3-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide

Product 1

HCID 668334012-acetamido-N-tert-butyl-2-(2-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-3-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamideYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acetaldehyde (0.06 mL, 1.1 mmol) and 2-acetamido-N-tert-butyl-2-(2-(1,2,3,4-tetrahydroisoquinolin-3-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (0.51 g, 1.0 mmol) in dichloromethane was stirred at room temperature for 1 h, then treated with sodium triacetoxyborohydride (0.63 g, 3 mmol). After stirring overnight, the reaction was quenched with 5% aq NaHCO3 (W/V) and extracted with dichloromethane. The organic layer was washed successively with 1 M HCl, sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated. Purification by flash chromatography (1% methanol in chloroform) gave 2-acetamido-N-tert-butyl-2-(2-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-3-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide as an oil (0.45 g, 83%). ESI MS found for C31H52BN3O4 m/z [b.e.542.7 (M+1)].

Workup

  1. customthe reaction was quenched with 5% aq NaHCO3 (W/V)
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed successively with 1 M HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (1% methanol in chloroform)

Sources & evidence

ORD record
ord-58d64d625cf34f93b6367a3cdae635bc
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

Loading…