4-(Benzoxazol-2-yl)benzyl bromide → HCID 54303745, compound

HRID 234746Notes

Reaction equation

HRID 234746 reaction equation
[C:1]([NH:20][CH:21]1[CH:28]2[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:30][C:22]1([OH:31])[CH2:23]3)[CH2:27]2)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[C:41]1[CH:48]=[CH:47][C:44]([CH2:45]Br)=[CH:43][CH:42]=1>C1COCC1>[C:1]([NH:20][CH:21]1[CH:28]2[CH2:27][CH:26]3[CH2:25][CH:24]([CH2:23][C:22]1([O:31][CH2:45][C:44]1[CH:47]=[CH:48][C:41]([C:33]4[O:32][C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=5[N:34]=4)=[CH:42][CH:43]=1)[CH2:30]3)[CH2:29]2)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 54340516N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

Product 1

HCID 54303745HCID 54303745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To KH (35%; 0.43 g; 0.0038 mole) in THF (10 ml) under N2 and cooled in ice is added N-trityl-1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (1.3 g; 0.0032 mole) and this mixture is stirred in an ice bath for 5 minutes and then at room temperature for an hour. To this mixture is added 4-(benzoxazol-2-yl)benzyl bromide all at once and an immediate yellow suspension develops. The reaction is stirred at room temperature for 4 hours, filtered and the filtrate stripped to dryness to give a solid residue. The components are separated on HPLC, eluting with 8% ethyl acetate/hexane to obtain N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7 ]decan-2-amine (m.p. 208°-210° C.) which is used directly in step C.

Workup

  1. waitat room temperature for an hour
  2. stirringThe reaction is stirred at room temperature for 4 hours
  3. filtrationfiltered
  4. customto give a solid residue
  5. customThe components are separated on HPLC
  6. washeluting with 8% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0ff51e7dd6af46788b4b24a003ae6262
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

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