Sodium hydride → HCID 19384420, compound

HRID 2399742Notes

Reaction equation

HRID 2399742 reaction equation
[OH:1][CH2:2][C:3]1([NH:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[H-].[Na+].[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1>C1COCC1>[C:16]1([C:9]([NH:8][C:3]2([CH2:2][O:1][CH2:43][C:42]3[CH:45]=[CH:46][C:39]([C:31]4[O:30][C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=5[N:32]=4)=[CH:40][CH:41]=3)[CH2:7][CH2:6][CH2:5][CH2:4]2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 19384400HCID 19384400, compound

Product 1

HCID 19384420HCID 19384420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-hydroxymethyl-1-triphenylmethylaminocyclopentane (2.95 g; 8.25 mmol) in 100 ml of THF is added sodium hydride (60%; 0.495 g; 12.38 mmol) and allowed to stir for 1 hr. To this mixture is then added 4-(benzoxazol -2-yl)benzyl bromide (1.90 g; 6.60 mmol) and heated to reflux for 48 hrs. The reaction mixture is quenched with H2O, concentrated in vacuo and flash chromatographed using 7:1; hexane:EtOAc to obtain 1-triphenylmethylamino(4-[benzoxazol-2-yl]benzyloxymethyl)cyclopentane which is used directly in the next step.

Workup

  1. temperatureto reflux for 48 hrs
  2. customThe reaction mixture is quenched with H2O
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

Sources & evidence

ORD record
ord-8f54cfee60d5483b9ffbdff19eed6d3b
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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