Methanol → HCID 21450032, compound

HRID 1578633Notes

Reaction equation

HRID 1578633 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23](=[O:37])[CH2:24][N:25]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CO>C(O)C>[CH2:16]([O:15][C:13]1[CH:12]=[C:11]([CH:23]([OH:37])[CH2:24][N:25]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 215597351-[3,5-Bis(phenylmethoxy)phenyl]-2-[(1,1-dimethylethyl)(phenylmethyl)amino]ethanone

Product 1

HCID 21450032HCID 21450032, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 18.3 g of 3',5'-dibenzyloxy-ω-(benzyl-t-butylamino)-acetophenone in ethanol were added 2 g of sodium borohydride. The reaction mixture was allowed to stand overnight. Some methanol was added and the solution was evaporated. To the residue was added water and 2-N sodium hydroxide solution and the water phase was extracted with ether. The ether phase was dried with magnesium sulphate. The ether was evaporated and an oil was collected, which crystallized on standing. M.p. 78°-79°C. The resulting 1-(3',5'-dibenzyloxyphenyl)-2-(benzyl-t-butylamino)-ethanol can be converted to the corresponding 1-(3',5'-dihydroxyphenyl)-2-(t-butylamino)-ethanol by replacing benzyl groups with hydrogen in a known manner.

Workup

  1. customthe solution was evaporated
  2. additionTo the residue was added water and 2-N sodium hydroxide solution
  3. extractionthe water phase was extracted with ether
  4. dry with materialThe ether phase was dried with magnesium sulphate
  5. customThe ether was evaporated
  6. customan oil was collected
  7. customwhich crystallized on standing

Sources & evidence

ORD record
ord-ae26c189f3884444b727fa62670c5160
Source dataset
uspto-grants-1976_02
Patent number
US03937838

Reaction notes

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