(2S)-2-(phenoxymethyl)oxirane → HCID 69818509, compound

HRID 2417409Notes

Reaction equation

HRID 2417409 reaction equation
[CH2:1]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]([CH2:29][C@@H:30]1[CH2:32][O:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[CH2:1]([N:8]([C@@H:9]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[CH2:10][OH:11])[CH2:32][C@H:30]([OH:31])[CH2:29][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 69818787HCID 69818787, compound

Product 1

HCID 69818509HCID 69818509, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2S)-2-(benzylamino)-3-(4-nitrophenyl)-1-propanol (1.15 g) and (2S)-2-(phenoxymethyl)oxirane (661 mg) in ethanol (9.2 ml) was heated to reflux for 3 hours. After allowed to cool to room temperature, the mixture was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give (2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl)amino]-3-(4-nitrophenyl)-1-propanol (1.17 g) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationthe mixture was concentrated
  4. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a4458832bd92402faf4f3aa27f9dac27
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

Loading…