Thionyl Chloride → (1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 380102Notes

Reaction equation

HRID 380102 reaction equation
O[CH2:2][CH2:3][CH2:4][C@@H:5]([NH:23][C@H:24]1[C:33]2[C:28](=[C:29]([O:34][Si:35]([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1)[C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.O=S(Cl)Cl>C(Cl)Cl>[C:11]1([C:9]2[N:10]=[C:6]([C@H:5]3[CH2:4][CH2:3][CH2:2][N:23]3[C@H:24]3[C:33]4[C:28](=[C:29]([O:34][Si:35]([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][CH2:25]3)[O:7][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54421594(1R)-1-[[(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl) butyl]amino]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54043965(1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-1-[[(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (2.6 g) in CH2Cl2 (50 ml) was added SOCl2 (3 ml). After being stirred for 12 hours, the solvent was removed. The residue was dissolved in N,N-dimethylformamide (DMF) (15 ml) and K2CO3 (2 g) was added to the solution. After being stirred for 4 hours at the room temperature, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.22 g).

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (DMF) (15 ml)
  3. additionK2CO3 (2 g) was added to the solution
  4. stirringAfter being stirred for 4 hours at the room temperature
  5. additionthe solution was poured into the mixture of ethyl acetate and water
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e895855c886a48638fe5bafdf3a314ea
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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