Tetrahydrofuran → HCID 28345409, compound

HRID 1987392Notes

Reaction equation

HRID 1987392 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C(Cl)Cl>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([S:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:4][OH:3])[CH2:11][CH2:10]2)(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 818681HCID 818681, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 28345409HCID 28345409, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the above ester (1.29 g, 4.79 mmol) in CH2Cl2 (20 mL) at 0° C. was added a solution of LiAlH4 in THF (1.0 M, 13.9 mL, 13.87 mmol) and the mixture was heated to reflux. After 1 h, the mixture was cooled back down to 0° C. and quenched with H2O (0.51 mL), 15% NaOH (0.51 mL), and H2O (1.53 mL). After stirring for 30 min, the reaction mixture was dried (MgSO4), filtered, and concentrated to afford [1-(toluene-4-sulfonyl)-piperidin-4-yl]-methanol as a clear oil (1.24 g, 100%). 1H NMR (CDCl3) δ 1.31-1.43 (m, 4H), 1.79 (d, 2H, J=12.0 Hz), 2.24 (t, 2H, J=12.0 Hz), 2.43 (s, 3H), 3.47 (d, 2H, J=6.0 Hz), 3.81 (d, 2H, J=12.0 Hz), 7.32 (d, 2H, J=6.0 Hz), 7.64 (d, 2H, J=6.0 Hz).

Workup

  1. temperaturethe mixture was heated to reflux
  2. customquenched with H2O (0.51 mL), 15% NaOH (0.51 mL), and H2O (1.53 mL)
  3. dry with materialthe reaction mixture was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc691bc859c94a10994e20f82335f159
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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