4-Methylmorpholine → HCID 59680073, compound

HRID 419866Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]2[O:14][C:15]3[C:16]([N:21]=2)=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]2[O:14][C:15]3[C:16]([N:21]=2)=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

In a typical run, 3-nitro-5-(oxazolo[4,5-b]pyridin-2-yl)benzoic acid (770 mg, 2.70 mmol) was suspended in 50 mL of anhydrous THF and cooled in an ice bath along with NMM (0.3 mL, 2.70 mmol). Isobutyl chloroformate (0.35 mL, 2.70 mmol) was added and the reaction mixture was stirred at 0° C. for 1 hour. A solution of NaBH4 (102 mg, 2.70 mmol) in 6 mL of water was then added at 0° C. and the reaction mixture was stirred at the same temperature for 45 min. It was then concentrated and the resulting residue was diluted with 10 mL of water. The aqueous layer was extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated to afford 500 mg of (3-nitro-5-oxazolo[4,5-b]pyridin-2-yl-phenyl)-methanol (68% yield, >95% pure by LC/MS).

Workup

stirringthe reaction mixture was stirred at the same temperature for 45 min
concentrationIt was then concentrated
additionthe resulting residue was diluted with 10 mL of water
extractionThe aqueous layer was extracted with CH2Cl2
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-b2d819d323374cde9aa8b6a869e5683d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093401B2

Reaction notes

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