Methanol → HCID 20058481, compound

HRID 2050565Notes

Reaction equation

HRID 2050565 reaction equation
[OH:1][CH:2]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:3][NH:4][C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]CC2C=CC=CC=2)=[C:17]([O:29]CC2C=CC=CC=2)[CH:16]=1)=O.B#B.CO>O1CCCC1>[OH:1][CH:2]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([OH:29])[C:18]([OH:21])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6328200DiboronHCID 20058553HCID 20058553, compound

Product 1

HCID 20058481HCID 20058481, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(2-hydroxy-2-phenylethyl)-N'-[2-(3,4-bis(phenylmethoxy)phenyl)ethyl]hexane-1,6-diamide prepared in an analogous manner to that described in Example 12(a) above (3.48 g) in dry tetrahydrofuran (100 ml) was stirred under a nitrogen atmosphere whilst diborane in tetrahydrofuran (30 ml of 1M solution) was added and then the solution heated to reflux for 6 hours. Methanol (100 ml) was added to the cooled solution and the mixture evaporated to dryness. The residue was dissolved in methanolic HCl (100 ml) and heated to reflux for 18 hours. The solution was evaporated to dryness and the residue recrystallised from ethanol to give the title compound, as the dihydrochloride salt, colorless prisms (1.3 g) mp 188°-9°.

Workup

  1. additionwas added
  2. temperaturethe solution heated
  3. temperatureto reflux for 6 hours
  4. customthe mixture evaporated to dryness
  5. dissolutionThe residue was dissolved in methanolic HCl (100 ml)
  6. temperatureheated
  7. temperatureto reflux for 18 hours
  8. customThe solution was evaporated to dryness
  9. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-adef1b8867734d44bfe0c5a8e0a4448e
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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