Methanol → HCID 53904472, compound

HRID 905304Notes

Reaction equation

HRID 905304 reaction equation
Br.[CH3:2][C:3]([NH:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:22]=1)=[O:20])([CH3:16])[CH2:4][NH:5][C:6](=[O:15])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BH4-].[Na+].CO.[Cl-].[Na+]>CC(O)C>[CH2:36]([O:35][C:23]1[CH:22]=[C:21]([CH:19]([OH:20])[CH2:18][NH:17][C:3]([CH3:2])([CH3:16])[CH2:4][NH:5][C:6](=[O:15])[CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 20446798HCID 20446798, compound

Product 1

HCID 53904472HCID 53904472, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-10 °C

Procedure

A suspension of 2[1,1-dimethyl-2-(2-phenoxyacetamido)ethyl]amino-3',4'-bis(benzyloxy)acetophenone hydrobromide (1.26 g.) in 2-propanol (10 ml.) was cooled to -10° C. and sodium borohydride (0.22 g.) was added in two portions interspersed by a a portion of methanol (10 ml.). The reaction mixture was allowed to warm to 10° C. After 30 minutes at this temperature, a saturated aqueous solution (100 ml.) of sodium chloride was added and the mixture was extracted with ether (3×100 ml.). The combined ether extracts were washed with water (100 ml.) and then brine (100 ml.), dried (MgSO4) and evaporated to give 1-[3,4-bis(benzyloxy)phenyl]-2-[1,1-dimethyl-2-(2-phenoxyacetamido)ethylamino]ethanol as a sticky residue (1.2 g.). This residue was dissolved in ethanol (30 ml.) and benzyl bromide (0.24 ml.) was then added. The mixture was hydrogenated at atmospheric pressure and temperature in the presence of 10% w/w palladium-on-carbon (0.4 g.) for 3 hours. The catalyst was separated by filtration, washed with ethanol (10 ml.) and the combined filtrate and washings evaporated to give 1-(3,4-dihydroxyphenyl)-2-[1,1-dimethyl-2-(2-phenoxyacetamido)ethylamino]ethanol hydrobromide as a foam (0.8 g.) having a satisfactory NRM spectrum and sufficiently pure for direct use in the above procedure.

Workup

  1. temperatureto warm to 10° C
  2. extractionthe mixture was extracted with ether (3×100 ml.)
  3. washThe combined ether extracts were washed with water (100 ml.)
  4. dry with materialbrine (100 ml.), dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-13c6ff9aadba492da8b6cb301e0ca972
Source dataset
uspto-grants-1983_12
Patent number
US04423070

Reaction notes

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