(2S)-2-(phenoxymethyl)oxirane → HCID 69329986, compound

HRID 1351872Notes

Reaction equation

HRID 1351872 reaction equation
[O:1]1[C@H:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[CH2:12]([NH:19][CH:20]1[CH2:26][CH2:25][CH2:24][C:23]2[CH:27]=[C:28]([OH:32])[C:29]([Cl:31])=[CH:30][C:22]=2[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[ClH:31].[CH2:12]([N:19]([CH2:2][C@H:3]([OH:1])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:20]1[CH2:26][CH2:25][CH2:24][C:23]2[CH:27]=[C:28]([OH:32])[C:29]([Cl:31])=[CH:30][C:22]=2[CH2:21]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 18007237HCID 18007237, compound

Product 1

HCID 69329986HCID 69329986, compoundYield 206.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2S)-1,2-epoxy-3-phenoxypropane (53 mg) (IL FARMACO, 50 (10), 643 (1995)) and N-benzyl-(3-chloro-6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)amine (89 mg) in ethanol (1 ml) was refluxed for 19 hours, cooled to room temperature and evaporated in vacuo. The residue was chromatographed (dichloromethane-methanol) by silica gel (2.9 g), and the eluate was treated with 4N hydrogen chloride in ethyl acetate to afford (2S)-1-[N-benzyl-N-(3-chloro-6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol hydrochloride (149 mg) as a colorless powder.

Workup

  1. customevaporated in vacuo
  2. customThe residue was chromatographed (dichloromethane-methanol) by silica gel (2.9 g)
  3. additionthe eluate was treated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-57a29f45733b422689fa89a28d728e43
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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