Potassium Hydroxide → 2-(6-Amino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester

HRID 898867Notes

Reaction equation

HRID 898867 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([S:12]C(=O)N(C)C)[CH:6]=[CH:5][C:4]=2[CH2:3]1.[OH-].[K+].Br[C:21]([CH3:30])([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[BH4-].[Na+]>CO>[C:25]([O:24][C:22](=[O:23])[C:21]([S:12][C:7]1[CH:6]=[CH:5][C:4]2[CH2:3][CH:2]([NH2:1])[CH2:11][CH2:10][C:9]=2[CH:8]=1)([CH3:30])[CH3:29])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 4311764Sodium borohydrideHCID 86594048dimethylthiocarbamic acid S-[6-amino-5,6,7,8-tetrahydronaphthalen-2-yl) ester

Product 1

HCID 688599032-(6-Amino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To dimethylthiocarbamic acid S-[6-amino-5,6,7,8-tetrahydronaphthalen-2-yl) ester (6.1 g; 24.4 mmol), dissolved in MeOH (25 mL) is added a solution of KOH (4.1 g; 73.2 mmol) in MeOH (25 mL) at RT. The solution is stirred at reflux for 5 h and cooled to RT. tert-Butyl 2-bromoisobutyrate (16.3 g; 73.2 mmol) is added to the solution and stirred for 16 h at RT. NaBH4 (9.2 g; 2.44 mol) is added and the reaction is stirred for an additional 48 h at RT. The reaction is quenched with H2O, the solvent evaporated under reduced pressure, and the crude residue partitioned between H2O and CH2Cl2. The aqueous phase is extracted with CH2Cl2 and the combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to afford 4.7 g (60%) of 2-(6-amino-5,6,7,8-tetrahydronaphthalen-2-ylsulfanyl)-2-methylpropionic acid tert-butyl ester as a brown oil. LC/MS: C181H27NO2S: m/z 266 (M+1)

Workup

  1. temperatureat reflux for 5 h
  2. stirringstirred for 16 h at RT
  3. stirringthe reaction is stirred for an additional 48 h at RT
  4. customThe reaction is quenched with H2O
  5. customthe solvent evaporated under reduced pressure
  6. customthe crude residue partitioned between H2O and CH2Cl2
  7. extractionThe aqueous phase is extracted with CH2Cl2
  8. dry with materialthe combined organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-230bbf27b3b64dd4bfcc1eeb1db823c3
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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