Benzoyl chloride → HCID 69300342, compound

HRID 2252384Notes

Reaction equation

HRID 2252384 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:27][CH:28]4[CH2:30][CH2:29]4)[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][C@H:19]4[C@@H:18]([N:31]1[CH2:35][CH2:34][CH2:33][C:32]1=[O:36])[CH2:17][CH2:16][C@@:15]35[OH:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.C1COCC1.[C:51](Cl)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C(=O)([O-])O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:27][CH:28]4[CH2:29][CH2:30]4)[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][C@H:19]4[C@@H:18]([N:31]1[CH2:35][CH2:34][CH:33]([C:51](=[O:58])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:32]1=[O:36])[CH2:17][CH2:16][C@@:15]35[OH:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 69300313HCID 69300313, compound

Product 1

HCID 69300342HCID 69300342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 mL of THF, 482 mg (0.96 mmol) of 1-(3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-morphinan-6α-yl)-pyrrolidin-2-one obtained in Example 36-1 was dissolved, and 6.9 mL (2.89 mmol) of 0.42 N LDA/THF solution was added thereto at −78° C., followed by stirring the mixture for 1 hour. Thereafter, 0.22 mL (1.92 mmol) of benzoyl chloride was added and the mixture was stirred for 2 hours. Aqueous saturated sodium hydrogen carbonate solution was then added to the reaction mixture, and the resulting mixture was extracted with chloroform. Organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to obtain 1-(3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-morphinan-6α-yl)-3-benzoyl-pyrrolidin-2-one as a crude product.

Workup

  1. customat −78° C.
  2. stirringthe mixture was stirred for 2 hours
  3. extractionthe resulting mixture was extracted with chloroform
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed81b5e689ae4adb95aae6d9fa88e49b
Source dataset
uspto-grants-2008_01
Patent number
US07320984B2

Reaction notes

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