Water → HCID 22808440, compound

HRID 1763865Notes

Reaction equation

HRID 1763865 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([C:14]1[CH:15]=[CH:16][C:17]2[CH2:18][C@H:19]3[N:30]([C:31]([CH:33]4[CH2:35][CH2:34]4)=O)[CH2:29][CH2:28][C@@:25]4([C:26]=2[CH:27]=1)[C@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24]4)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[O:7]([C:14]1[CH:15]=[CH:16][C:17]2[CH2:18][C@H:19]3[N:30]([CH2:31][CH:33]4[CH2:35][CH2:34]4)[CH2:29][CH2:28][C@@:25]4([C:26]=2[CH:27]=1)[C@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24]4)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 53861772HCID 53861772, compound

Product 1

HCID 22808440HCID 22808440, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.4 g of lithium aluminum hydride in 20 ml of anhydrous tetrahydrofuran was added dropwise, 4.6 g (0.011 mol) of (-)-3-phenoxy-N-cyclopropylcarbonylmorphinan in 30 ml of anhydrous tetrahydrofuran over a period of 15 minutes. After the mixture had been refluxed under nitrogen for 16 hours, it was cooled to room temperature and water was added dropwise. The resulting suspension was filtered and the filtrate was concentrated. The residue was partitioned between ether and 4 N hydrochloric acid. The acidic phase was made basic with concentrated ammonium hydroxide and the aqueous suspension was extracted with ether. The ether solution was washed with water and dried. Removal of the ether under reduced pressure afforded 2.6 g (59%) of the product (-)-3-phenoxy-N-cyclopropylmethylmorphinan. For analysis, a sample of this compound was distilled, bp 190°200°/0.1mmHg, [α]25D -89.07° (c 0.99, MeOH).

Workup

  1. additionwas added dropwise
  2. temperatureAfter the mixture had been refluxed under nitrogen for 16 hours
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was partitioned between ether and 4 N hydrochloric acid
  6. extractionthe aqueous suspension was extracted with ether
  7. washThe ether solution was washed with water
  8. customdried
  9. customRemoval of the ether under reduced pressure

Sources & evidence

ORD record
ord-769fd0784d2a49f491ae18e46fdf6dd1
Source dataset
uspto-grants-1978_09
Patent number
US04113729

Reaction notes

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