Aminoacetaldehyde dimethyl acetal → HCID 178495886, compound

HRID 1041783Notes

Reaction equation

HRID 1041783 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][C:14](SC)=[N:13][C:12]=2[CH:20]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH2:25][NH2:26]>C(O)C>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][C:14]([NH:26][CH2:25][CH:24]([O:27][CH3:28])[O:23][CH3:22])=[N:13][C:12]=2[CH:20]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 57853869HCID 57853869, compound

Product 1

HCID 178495886HCID 178495886, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2-methylsulfanyl-4,5-dihydro-3H-benzo[b]azepin-8-yl)-carbamic acid tert-butyl ester (2.2 g, 7.2 mmol) and 2,2-dimethoxyethanamine (1.0 g, 9.5 mmol) in ethanol (200 mL) was heated in an oil bath at 100° C. for 14 hours. The mixture was concentrated and purified by silica gel chromatography with DCM/MeOH (9:1) to give [2-(2,2-dimethoxy-ethylamino)-4,5-dihydro-3H-benzo[b]azepin-8-yl]-carbamic acid tert-butyl ester (1.6 g, 4.4 mmol, 61%): 1H NMR (300 MHz, CDCl3) δ 7.1 (m, 2H), 6.93 (s, 1H), 6.48 (s, 1H), 4.69 (t, 1H), 3.66 (d, 2H), 3.54 (s, 6H), 2.61 (t, 2H), 2.2 (br, 4H), 1.61 (s, 9H); MS (m/e) 364 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography with DCM/MeOH (9:1)

Sources & evidence

ORD record
ord-f05bfdaa7c5b40b3af7d3ed494eee704
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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