Benzyl Bromide → HCID 69300327, compound

HRID 2252385Notes

Reaction equation

HRID 2252385 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.[CH2:51](Br)[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]([CH2:51][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 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 69299180HCID 69299180, compound

Product 1

HCID 69300327HCID 69300327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 mL of THF, 145 mg (0.35 mmol) of 1-(3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-morphinan-6β-yl)-pyrrolidin-2-one obtained in Example 47-1 was dissolved, and 2.84 mL (1.02 mmol) of 0.36 N LDA/THF solution was added at −78° C., followed by stirring the mixture for 1 hour. Thereafter, 0.10 mL (0.87 mmol) of benzyl bromide was added thereto and the resulting mixture was stirred for 3 hours. To this reaction solution, aqueous saturated sodium hydrogen carbonate solution was added 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-6β-yl)-3-benzyl-pyrrolidin-2-one as a crude product.

Workup

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

Sources & evidence

ORD record
ord-97e3e32cc1944cdaa032015503c0002b
Source dataset
uspto-grants-2008_01
Patent number
US07320984B2

Reaction notes

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