Sodium hydride → HCID 66956451, compound

HRID 2066663Notes

Reaction equation

HRID 2066663 reaction equation
[CH3:1][C@@:2]1([CH2:14][OH:15])[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4][CH2:3]1.[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.[H-].[Na+]>>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:15][CH2:14][C@:2]2([CH3:1])[O:7][C:6]3=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]3[CH2:4][CH2:3]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 66956706HCID 66956706, compound

Product 1

HCID 66956451HCID 66956451, compoundYield 57%

Procedure

Alkylation of (R)-alcohol 159 with 4-bromobenzyl bromide (1.3 equiv.) and NaH (1.5 equiv.) as in Example 2UU above for 3 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 1% EtOAc/CH2Cl2, gave (7R)-7-{[(4-bromobenzyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (160) (349 mg, 57%) as a white solid: mp (CH2Cl2/hexane) 157-159° C.; 1H NMR (CDCl3) δ 7.46 (dt, J=8.3, 2.0 Hz, 2H), 7.39 (s, 1H), 7.12 (br d, J=8.3 Hz, 2H), 4.50 (s, 2H), 4.09 (ddd, J=12.5, 6.9, 6.0 Hz, 1H), 4.01 (ddd, J=12.5, 7.0, 6.0 Hz, 1H), 3.62 (d, J=10.2 Hz, 1H), 3.58 (d, J=10.2 Hz, 1H), 2.37 (ddd, J=14.4, 7.0, 6.0 Hz, 1H), 2.10 (ddd, J=14.4, 6.9, 6.1 Hz, 1H), 1.46 (s, 3H); [α]D27 30.0° (c 1.00, CHCl3); HRFABMS calcd for C15H17BrN3O4 m/z [M+H]+ 384.0382, 382.0402. found 384.0385, 382.0398.

Workup

  1. customabove for 3 h
  2. washeluting with CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-2c73e98bbeb344a198b826d81dbf5bb0
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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