Water → 1-[2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-2-hydroxy-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 1741385Notes

Reaction equation

HRID 1741385 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][NH:19]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:23]([O:40][C:41]1[CH:50]=[CH:49][CH:48]=[C:47]2[C:42]=1[CH2:43][CH2:44][CH:45]1[O:51][CH:46]12)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C.O>O1CCCC1>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH:46]3[C:47]4[C:42](=[C:41]([O:40][Si:23]([C:36]([CH3:38])([CH3:37])[CH3:39])([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:50]=[CH:49][CH:48]=4)[CH2:43][CH2:44][CH:45]3[OH:51])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 183672762-(4,5-Diphenyloxazol-2-yl)pyrrolidineHCID 183674385-Tert-butyldiphenylsilyloxy-1,2-epoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 183673291-[2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-2-hydroxy-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4,5-diphenyloxazol-2-yl)pyrrolidine (0.66 g) and 5-tert-butyldiphenylsilyloxy-1,2-epoxy-1,2,3,4-tetrahydronaphthalene (0.6 g) in tetrahydrofuran (10 ml) was added Ti[O-CH(CH3)2 ]4 (0.66 ml) at room temperature. After being stirred for 5 days at the same temperature, the mixture 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 1-[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-2-hydroxy-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (0.31 g). MS (m/z): 691 (M+) IR (Neat): 3300 cm-1NMR (CDCl3, δ): 1.07 (9H, s), 1.7-2.4 (6H, m), 2.6-3.3 (2H, m), 3.4-3.6 (2H, m), 4.1-4.4 (2H, m), 6.28 (1H, d, J=8.0 Hz), 6.75 (1H, t, J=8.0 Hz), 6.88 (1H, d, J=8.0 Hz), 7.3-7.8 (20H, m)

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-60fe60aaafef4eb7a9cb881b2b5df5e1
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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