Methanol → HCID 15198019, compound

HRID 234740Notes

Reaction equation

HRID 234740 reaction equation
[C:1]([NH:20][CH:21]1[CH:28]2[CH2:29][CH:24]3[CH2:25][C:26]([OH:31])([CH2:30][CH:22]1[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.CO>C1COCC1>[C:1]([NH:20][CH:21]1[CH:22]2[CH2:23][CH:24]3[CH2:25][C:26]([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)([CH2:27][CH:28]1[CH2:29]3)[CH2:30]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

5

Reactant 3

HCID 887MethanolHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 54395449HCID 54395449, compound

Product 1

HCID 15198019HCID 15198019, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To KH (35%; (0.34 g; 0.0029 mole) in THF (8 ml) under N2 and cooled in an ice bath is added N-trityl-5-hydroxytricyclo-[3.3.1.13,7 ]decan-2-amine (1.0 g; 0.0025 mole) This forms a pale yellow solution and is stirred at room temperature for 1 hour. The reaction mixture is then cooled in ice and 4-(benzoxazol-2-yl)benzyl bromide (0.7 g; 0.0025 mole) is added all at once. The mixture is stirred for 1/2 hour with ice cooling and then 31/2 hours at room temperature then cooled in ice and MeOH is added to quench the KH. The mixture is evaporated to dryness. Purification is accomplished on HPLC eluting with a gradient system staring with 10% and ending with 20% ethyl acetate/hexane to obtain N-trityl-5-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7 ]decan-2-amine which is used directly in step F.

Workup

  1. temperatureThe reaction mixture is then cooled in ice
  2. stirringThe mixture is stirred for 1/2 hour with ice cooling
  3. temperature31/2 hours at room temperature then cooled in ice
  4. customto quench the KH
  5. customThe mixture is evaporated to dryness
  6. customPurification
  7. washeluting with a gradient system

Sources & evidence

ORD record
ord-5fa2dd0866c642e48a6ba1f0bb23fe99
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

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