Tetrahydrofuran → (3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

HRID 1492444Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[C@@H:7]2[O:8][C@@H:6]2[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.O1CCCC1.[OH-].[NH4+:22]>C(O)C>[NH2:22][C@@H:6]1[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3][C:2]([CH3:15])([CH3:1])[C@H:7]1[OH:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile (3.0 g, 15.0 mmol, compound of example 1, part A) in ethanol (30 mL) and tetrahydrofuran (30 mL) was added ammonium hydroxide (30 mL) and the reaction mixture was heated at 50° C. in a pressure bottle for 16 hours. Most of the solvent was evaporated and the residue was dissolved in 1N hydrochloric acid. It was extracted with ether and the organic extracts were discarded. The aqueous layer was made basic by the addition of 1N sodium hydroxide and extracted with chloroform. The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to yield (3S-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H- 1-benzopyran-6-carbonitrile (2.8 g), as a colorless foam. This material was used for the next reaction without further purification.

Workup

customMost of the solvent was evaporated
dissolutionthe residue was dissolved in 1N hydrochloric acid
extractionIt was extracted with ether
additionThe aqueous layer was made basic by the addition of 1N sodium hydroxide
extractionextracted with chloroform
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-e009aa87e1964c69870f9f5318a35f4a
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374643

Reaction notes

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