Sodium hydride → HCID 66957365, compound

HRID 2066665Notes

Reaction equation

HRID 2066665 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 66956709HCID 66956709, compound

Product 1

HCID 66957365HCID 66957365, compoundYield 61%

Procedure

Alkylation of (S)-alcohol 162 with 4-bromobenzyl bromide (1.35 equiv.) and NaH (1.55 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 (7S)-7-{[(4-bromobenzyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (163) (373 mg, 61%) as a white solid: mp (CH2Cl2/hexane) 159-161° C.; 1H NMR (CDCl3) δ 7.46 (dt, J=8.4, 2.1 Hz, 2H), 7.39 (s, 1H), 7.12 (dt, J=8.4, 2.1 Hz, 2H), 4.50 (s, 2H), 4.09 (ddd, J=12.5, 7.0, 5.8 Hz, 1H), 4.01 (ddd, J=12.5, 7.1, 5.9 Hz, 1H), 3.62 (d, J=10.2 Hz, 1H), 3.58 (d, J=10.2 Hz, 1H), 2.37 (ddd, J=14.4, 7.1, 5.9 Hz, 1H), 2.10 (ddd, J=14.5, 7.0, 5.9 Hz, 1H), 1.46 (s, 3H); [α]D27−32.0° (c 1.00, CHCl3); HRFABMS calcd for C15H17BrN3O4m/z [M+H]+ 384.0382, 382.0402. found 384.0374, 382.0393.

Workup

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

Sources & evidence

ORD record
ord-a3395293041f43fc9e6dfde1a7a21961
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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