Diethyl Ether → HCID 67073443, compound

HRID 2253029Notes

Reaction equation

HRID 2253029 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH:14]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][C:17]=2[F:31])O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:32]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH:14]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][C:17]=2[F:31])[Br:32])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67073052HCID 67073052, compound

Product 1

HCID 67073443HCID 67073443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.5 g of ((S)-2-[(4-benzyloxy-2,5-difluoro-phenyl)-hydroxy-methyl]-morpholine-4-carboxylic acid tert-butyl ester in dichloromethane (90 ml) was added with cooling (0-5° C.) tetrabromomethane (12.5 g) and afterwards triphenylphosphine (13.5 g) in small portions. Stirring continued for 1 hour at room temperature before the mixture was added dropwise to diethyl ether (600 mL). Solids were removed by filtration and the filtrate was concentrated in vacuo. The residue was then purified by column chromatography (heptane-ethyl acetate (3:1)/silica gel) to give 5.6 g of the title compound.

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was then purified by column chromatography (heptane-ethyl acetate (3:1)/silica gel)

Sources & evidence

ORD record
ord-e551579a49474d7198c5c2a3fe32e69b
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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