Benzene → HCID 22867072, compound

HRID 1901165Notes

Reaction equation

HRID 1901165 reaction equation
[NH2:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].O=[C:12]([CH3:24])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>O.CO>[OH:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH:12]([NH:1][CH2:2][C@H:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[OH:4])[CH3:24])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 643217(1S)-2-amino-1-phenylethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 218321652-[4-(2-Oxopropoxy)phenyl]ethanol

Product 1

HCID 22867072HCID 22867072, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A procedure similar to that described in Example 3 was repeated, except that 1.4 g of 2-amino-1(S)-phenylethanol (prepared as described in Preparation 16), 2.4 g of 2-[4-(2-oxopropoxy)phenyl]ethanol (prepared as described in Preparation 7), 100 ml of benzene, 100 ml of absolute methanol and 0.95 g of sodium cyanoborohydride were used and that, after the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was then concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 30:1 by volume mixture of ethyl acetate and ethanol as the eluent. 0.53 g of the title compound was obtained as crystals, melting at 93°-96° C. (after recrystallization from ethyl acetate).

Workup

  1. customthat, after the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract was then concentrated by evaporation under reduced pressure
  4. customthe concentrate was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and ethanol as the eluent

Sources & evidence

ORD record
ord-c0f5ace7e33946cea577abd11d0b62e6
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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