Borane;tetrahydrofuran → 2-(6-Ethylamino-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester

HRID 2104264Notes

Reaction equation

HRID 2104264 reaction equation
[C:1]([O:5][C:6](=[O:27])[C:7]([S:10][C:11]1[C:20]([O:21][CH3:22])=[CH:19][C:18]2[CH2:17][CH:16]([NH:23][C:24](=O)[CH3:25])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1.C(OC(=O)C(SC1C=CC2CC(NCC)CCC=2C=1)(C)C)(C)(C)C>C1COCC1>[C:1]([O:5][C:6](=[O:27])[C:7]([S:10][C:11]1[C:20]([O:21][CH3:22])=[CH:19][C:18]2[CH2:17][CH:16]([NH:23][CH2:24][CH3:25])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 688122962-(6-Acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl esterHCID 688125622-(6-Ethylamino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester

Product 1

HCID 688129392-(6-Ethylamino-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(6-acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester (0.68 g; 1.74 mmol) in THF (15 mL) was added a solution of 1.0 M borane-THF (15 mL), dropwise at room temperature. The reaction mixture was allowed to stir for 18 h at room temperature, then carefully quenched with MeOH (10 mL) and the solvent evaporated under reduced pressure. The residual oil was further azeotroped with MeOH (3×) to yield a mixture of 2-(6-ethylamino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester and it's borane complex as an oil.

Workup

  1. customdropwise at room temperature
  2. customcarefully quenched with MeOH (10 mL)
  3. customthe solvent evaporated under reduced pressure
  4. customThe residual oil was further azeotroped with MeOH (3×)
  5. customto yield

Sources & evidence

ORD record
ord-29170429b87f4a12aae44668fd304936
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Reaction notes

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