Methanol → (1R,4R)-4-(tert-Butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine

HRID 605853Notes

Reaction equation

HRID 605853 reaction equation
[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([NH:29]C(=O)C(F)(F)F)[CH2:21][CH2:20]1)([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.CO.C(=O)([O-])[O-].[K+].[K+]>O.CCOC(C)=O>[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([NH2:29])[CH2:21][CH2:20]1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59704873N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 59704938(1R,4R)-4-(tert-Butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amineYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 ml round bottom flask containing 4 g (8.0 mmol) of N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamide was added 160 ml of MeOH. To this solution was added a solution of 8.34 g (60 mmol) potassium carbonate in 16 ml of water. The reaction mixture was stirred at room temp overnight. The reaction mixture was diluted with 150 ml EtOAc, and after separation, the aqueous phase was extracted several times with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo to afford 3.09 g (96%) of the title compound, whose purity was good enough to use crude. (Note: On separate occasion, this hydrolysis became sluggish, and 30 ml of 3M NaOH was added, upon which the reaction was completed in a few hours.)

Workup

  1. customafter separation
  2. extractionthe aqueous phase was extracted several times with EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c30f58f306784ae5acc9d64681849752
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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