Ethyl Acetate → 2-[2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalen

HRID 1741384Notes

Reaction equation

HRID 1741384 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][C:45](=O)[CH2:46]2)([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.[BH3-]C#N.[Na+].C(OCC)(=O)C>CO.C(O)(=O)C.O>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH:45]3[CH2:44][CH2:43][C:42]4[C:47](=[CH:48][CH:49]=[CH:50][C:41]=4[O:40][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:46]3)[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

8

Reactant 4

HCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 183672762-(4,5-Diphenyloxazol-2-yl)pyrrolidineHCID 183673695-Tert-butyldiphenylsilyloxy-2-oxo-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 183672402-[2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalenYield 99.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(4,5-diphenyloxazol-2-yl)pyrrolidine (0.6 g) and 5-tert-butyldiphenylsilyloxy-2-oxo-1,2,3,4-tetrahydronaphthalene (0.5 g) in a mixture of methanol (10 ml) and acetic acid (2 ml) was added NaBH3CN (250 mg) at room temperature. After being stirred for 2 hours 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 2-[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalen (0.84 g). MS (m/z): 676 (M+) IR (Neat): 1580 cm-1NMR (CDCl3, δ): 1.08 (9H, s), 1.5-2.4 (6H, m), 2.6-3.3 (6H, m), 4.42 (1H, m), 6.10 (1H, m), 6.4-6.7 (2H, m), 7.2-7.8 (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-c6dcc1fb67244e669f2699a549f26a3b
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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