4-Phenoxybenzaldehyde → (S)-4-(4-phenoxybenzyl)-2-phenylmorpholine

HRID 2076803Notes

Reaction equation

HRID 2076803 reaction equation
O[CH2:2][CH2:3][NH:4][CH2:5][C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7].[O:14]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[O:14]([C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:4]2[CH2:3][CH2:2][O:7][C@@H:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:5]2)=[CH:27][CH:28]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 661394-PhenoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57849522(S)-2-(2-Hydroxy-ethylamino)-1-phenyl-ethanol

Product 1

HCID 24955878(S)-4-(4-phenoxybenzyl)-2-phenylmorpholineYield 8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

200 mg of (S)-2-Phenyl-morpholine (see synthesis in Example 1) was dissolved in 2 mL of dichloroethane and 253 μL of 4-Phenoxy-benzaldehyde was added. The reaction was stirred at room temperature 30 minutes and then 467 mg of sodium triacetoxyborohydride was added. The reaction was stirred overnight at room temperature. The reaction solution was then washed with aqueous saturated sodium bicarbonate solution several times followed by a brine wash. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparatory chromatography gave the title compound. 8% yield. EI m/z 346=MH+

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. washThe reaction solution was then washed with aqueous saturated sodium bicarbonate solution several times
  3. washwash
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by preparatory chromatography

Sources & evidence

ORD record
ord-5a14671aba1447f1b1c47515c924e224
Source dataset
uspto-grants-2011_04
Patent number
US07928103B2

Reaction notes

Loading…