Methanol → HCID 53730484, compound

HRID 234744

Reaction equation

HRID 234744 reaction equation
[C:1]([NH:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][C:23]([OH:31])([CH2:24]3)[CH2:22]1)[CH2:28]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.CO>C1COCC1>[C:1]([NH:20][C:21]12[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][C:23]([O:31][CH2:45][C:44]4[CH:47]=[CH:48][C:41]([C:33]5[O:32][C:36]6[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=6[N:34]=5)=[CH:42][CH:43]=4)([CH2:29]3)[CH2:22]1)[CH2:30]2)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 54523384N-trityl-3-hydroxytricyclo-[3.3.1.13,7]decan-1-amine

Product 1

HCID 53730484HCID 53730484, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To KH (35%; 0.35 g; 0.003 mole) in THF (8 ml) under N2 and cooled to 0° C. is added N-trityl-3-hydroxytricyclo-[3.3.1.13,7 ]decan-1 -amine (1 g; 0.0025 mole) of all at once. The reaction is stirred for 5 minutes with ice cooling then at room temperature for an hour, developing into a clear yellow solution. Then 4-(benzoxazol-2-yl)benzyl bromide (0.70 g; 0.0025 mole) is added and the reaction cooled in ice for 10 minutes and stirred at room temperature for 4 hours. Methanol is added to quench any KH, then the reaction is filtered and evaporated to dryness. HPLC is used to purify the product (eluting with 10% ethyl acetate/hexane) to obtain N-trityl-3-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7 ]decan-1-amine (m.p. 174°-177° C.) which is used directly in step D.

Workup

  1. waitat room temperature for an hour
  2. temperaturethe reaction cooled in ice for 10 minutes
  3. stirringstirred at room temperature for 4 hours
  4. customto quench any KH
  5. filtrationthe reaction is filtered
  6. customevaporated to dryness
  7. customto purify
  8. washthe product (eluting with 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-826a2e324c84418a9ccc11a26eb0c153
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Linked notes

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