tert-Butyl 5-((6-(benzyloxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → tert-Butyl 5-((6-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710385Notes

Reaction equation

HRID 710385 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:19][C:20]1([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)[CH2:13][CH2:12]2)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:19][C:20]1([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)[CH2:13][CH2:12]2

Participants

4

Reactant 1

HCID 86661787tert-Butyl 5-((6-(benzyloxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 86661788tert-Butyl 5-((6-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Example 38, Step E, (0.13 g; 0.27 mmol) and 10% Pd/C (0.3 g) in EtOAc (15 ml) was vigorously stirred at room temperature for 3 h under H2 (balloon). The catalyst was removed by filtration through the Celite pad, washed with CH2Cl2 (2×10 ml) and combined filtrates were evaporated to dryness under reduced pressure to give the title compound (0.105 g; 99%) as colourless solid. 1H-NMR (CDCl3) 1.4 (s, 3H); 1.42 (s, 9H); 1.44 (s, 3H); 2.7-2.85 (m, 4H); 2.91 (s, 2H); 3.8 (s, 2H); 3.82 (d, 2H, J=11.6 Hz); 4.05 (d, 2H, J=11.6 Hz); 4.98 (broad s, 1H); 5.5 broad s, 1H); 6.52-6.6 (m, 2H); 6.76 (d, 1H, J=8.2 Hz).

Workup

  1. customThe catalyst was removed by filtration through the Celite pad
  2. washwashed with CH2Cl2 (2×10 ml)
  3. customwere evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f559cbfb1ecf403c927611f9261cd2b0
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…