Borane;tetrahydrofuran → (1S)-1-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 1741361Notes

Reaction equation

HRID 1741361 reaction equation
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][C:24]2=[O:29])([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.C1(C2(C3C=CC=CC=3)OB(C)N3CCC[C@H]23)C=CC=CC=1.O1CCCC1.B>C1COCC1>[OH:29][C@@H:24]1[C:25]2[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 224673025-Tert-butyldiphenylsilyloxy-1-tetralone

Product 1

HCID 56983638(1S)-1-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneYield 109.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-t-butyldiphenylsilyloxy-1-tetralone (2.9 g) and (R)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (2.3 g) in THF (5 ml) was added borane tetrahydrofuran complex (7.1 ml, 1 M solution in THF) at -18° C. After being stirred for 30 minutes, the reaction was quenched with 1N HCl solution. The mixture was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1S)-1-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (3.2 g). MS (m/z): 401 (M+ -1) NMR (CDCl3, δ): 1.10 (9H, s), 1.8-2.2 (4H, m), 2.6-3.1 (2H, m), 4.79 (1H, t, J=4.8 Hz), 6.30 (1H, d, J=8 Hz), 6.77 (1H, t, J=8 Hz), 6.97 (1H, d, J=8 Hz), 7.3-7.9 (10H, m) HPLC; chiralcel AD, 2% isopropanol/hexane, 20.3 ml/min

Workup

  1. customthe reaction was quenched with 1N HCl solution
  2. additionThe mixture was poured into a mixture of ethyl acetate and water
  3. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-eb6d5c96fbf74db38081eeecb2830ece
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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