Diisopropyl Ether → HCID 178486612, compound

HRID 480476Notes

Reaction equation

HRID 480476 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C:15]([C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])[CH:7]=[CH:6]2.CC1(C)COP(=O)(O)OC1C1C=CC=CC=1.C(OC(C)C)(C)C>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C@@:15]([C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 4156748ACMC-20apmuHCID 178486613HCID 178486613, compound

Product 1

HCID 178486612HCID 178486612, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol(485 mg) and (−)-5,5-dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide (653 mg) were dissolved in methanol (4 mL). Diisopropyl ether (3 mL) was added and the resulting clear solution was left at room temperature for 5 h to give needles. The needles were washed with a mixed solution of methanol-diisopropyl ether (1:3, 4 mL) and diisopropyl ether (1 mL) and then dried to give the titled compound (362 mg) as colorless needles. Optical purity; >99% ee (Chiralcel OJ-R, manufactured by Daicel Chemical Industries, Ltd.).

Workup

  1. customto give needles
  2. washThe needles were washed with a mixed solution of methanol-diisopropyl ether (1:3, 4 mL) and diisopropyl ether (1 mL)
  3. customdried

Sources & evidence

ORD record
ord-922fde075c4a4d31821f5184ed9bd1a1
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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