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

HRID 1363228Notes

Reaction equation

HRID 1363228 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:24][C@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@H:28]([NH:35]C(=O)C(F)(F)F)[CH2:27][CH2:26]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.CO.CCOC(C)=O>[Si:7]([O:24][C@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@H:28]([NH2:35])[CH2:27][CH2:26]1)([C:20]([CH3:22])([CH3:23])[CH3:21])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 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%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (8.3 g) in water (16 mL) was added to a solution of N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamide (4 g) in MeOH (160 mL). The reaction mixture was stirred at room temp overnight then diluted with EtOAc (150 mL), 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 3.1 g of the title compound, whose purity was good enough to use crude. 1H-NMR (300 MHz, CDCl3) □ 7.7 (d, 2H), 7.6 (d, 2H), 7.4 (m, 7H), 7.2 (m, 3H), 4.8 (t, 1H), 4.2 (t, 1H), 3.8 (broad s, 2H), 2.4 (m, 1H), 1.8 (m, 2H), 1.6 (m, 1H) ppm.

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-bd5b2994bcc144eb9a31fb8c7f1f3c6d
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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