Methanol → HCID 86594704, compound

HRID 553561Notes

Reaction equation

HRID 553561 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][CH:24]=O)[CH2:17]1.[BH4-].[Na+].C[OH:29]>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH:18]([O:22][C@@H:23]([OH:29])[CH3:24])[CH2:17]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59820029HCID 59820029, compound

Product 1

HCID 86594704HCID 86594704, compound

Procedure

2.3 g of 4-((1R,3S)-3-(allyloxycyclohexyloxymethyl)-5-methyl-2-m-tolyloxazole are dissolved in 65 ml of methyl tert-butyl ether and, at 0° C., 65 ml of water, 4.4 g of sodium metaperiodate and 3.3 ml of a 2.5% strength solution of osmium tetroxide in tert-butanol are added. After 20 min, the mixture is slowly warmed to 40° C. After 2 h, a further 700 mg of sodium metaperiodate were added and the mixture was stirred at 45° C. for 2 h. 140 ml of sat. sodium thiosulfate solution were added and the mixture was extracted with methyl tert-butyl ether. The combined organic phases are dried over sodium sulfate and the solvent is removed under reduced pressure. This gives 2-((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]acetaldehyde as a colorless oil. C20H25NO4 (343.43), MS (ESI): 344 (M+H+). 2-((1R,3S)-[3-(5-Methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]acetaldehyde is, as a crude product, taken up in 60 ml of dry methanol, and 300 mg of sodium borohydride are added. After 1.5 h, the mixture is quenched with 3 ml of acetone and concentrated. The residue is taken up in 50 ml of ethyl acetate/50 ml of sat. sodium bicarbonate solution, and the org. phase is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is then purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:3). This gives 1.6 g of 2-((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethanol as a colorless oil. C20H27NO4 (345.44), MS (ESI): 346 (M+H+).

Workup

  1. customthe mixture is quenched with 3 ml of acetone
  2. concentrationconcentrated
  3. dry with materialphase is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is then purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:3)

Sources & evidence

ORD record
ord-29f7b0ecfc3c4b81b4a1ce8f7ea62ddc
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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