Hydrochloric Acid → HCID 22467283, compound

HRID 1934562Notes

Reaction equation

HRID 1934562 reaction equation
[Si:1]([O:18][C:19]1[C:24]2[CH2:25][CH2:26][CH2:27][C:28]3([CH2:31][OH:32])[CH2:30][CH:29]3[C:23]=2[CH:22]=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([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.[C:33]1([N:39]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:40](Cl)=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>N1C=CC=CC=1>[C:33]1([N:39]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:40](=[O:41])[O:32][CH2:31][C:28]23[CH2:30][CH:29]2[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:24]=2[CH2:25][CH2:26][CH2:27]3)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65741N,N-Diphenylcarbamic chlorideHCID 22467306HCID 22467306, compound

Product 1

HCID 22467283HCID 22467283, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [5-(tert-butyldiphenylsilyloxy)-1,1a,2,3,4,8b-hexahydrobenzo[a]cyclopropa[c]cyclohepten-1a-yl]methanol (639 mg) and diphenylcarbamoyl chloride (1.0 g) in pyridine (6 ml) was stirred at 100° C. for 22 hours. After cooling, the reaction mixture was poured into 6N-hydrochloric acid (16 ml) under ice-cooling. The resultant was extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogencarbonate solution, water, and then brine. It was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 12:1 to 10:1) to give [5-(tert-butyldiphenylsilyloxy)-1,1a,2,3,4,8b -hexahydrobenzo[a]cyclopropa[c]cyclohepten-1a-yl]methyl N,N-diphenylcarbamate (782.2 mg) as an amorphous solid.

Workup

  1. temperatureAfter cooling
  2. temperaturecooling
  3. extractionThe resultant was extracted with EtOAc
  4. washThe organic layer was washed with water, saturated sodium hydrogencarbonate solution, water
  5. dry with materialIt was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 12:1 to 10:1)

Sources & evidence

ORD record
ord-23f4bb1a39db47f18df25a86cba246d5
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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