Tetrahydrofuran → HCID 10901772, compound

HRID 328351Notes

Reaction equation

HRID 328351 reaction equation
[O:1]1[C@@:15]23[C@:6]4([CH2:18][CH2:17][NH:16][C@@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:19][CH3:20])=[CH:8][C:7]4=2)[CH2:5][CH2:4][CH2:3][CH:2]13.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:1][C@:15]12[C@@H:14]3[NH:16][CH2:17][CH2:18][C@:6]1([C:7]1[CH:8]=[C:9]([O:19][CH3:20])[CH:10]=[CH:11][C:12]=1[CH2:13]3)[CH2:5][CH2:4][CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 86733977HCID 86733977, compound

Product 1

HCID 10901772HCID 10901772, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 800 mg. of the amine-epoxide (XX) in 10 ml. of tetrahydrofuran was added dropwise at room temperature, to a suspension of 50 mg. of lithium aluminum hydride in 5 ml. of dry tetrahydrofuran. After the addition had been completed, the reaction mixture was stirred and refluxed during fifteen minutes. Work up as usual yielded 700 mg. of an oil which was dissolved in ether and the resulting solution was filtered through a celitecharcoal mixture. The filtrate was treated with a saturated solution of hydrochloric acid in ether to yield 720 mg. of a white hydrochloride salt which after recrystallization from methanol melted at 243°-44° C.(dec.). The IR and NMR were consistent with the structure.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed during fifteen minutes
  3. customWork up as usual yielded 700 mg
  4. filtrationthe resulting solution was filtered through a celitecharcoal mixture
  5. additionThe filtrate was treated with a saturated solution of hydrochloric acid in ether
  6. customto yield 720 mg
  7. customof a white hydrochloride salt which after recrystallization from methanol melted at 243°-44° C.(dec.)

Sources & evidence

ORD record
ord-73174043be9e4cb1adc494f335055f1e
Source dataset
uspto-grants-1977_04
Patent number
US04017497

Reaction notes

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