HCID 67412184, compound → HCID 67413604, compound

HRID 1526411Notes

Reaction equation

HRID 1526411 reaction equation
C([O:8][CH2:9][CH2:10][C@@H:11]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])=[CH:21][CH:20]=2)[CH2:12][C:13]([O:15][CH3:16])=[O:14])C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[OH:8][CH2:9][CH2:10][C@@H:11]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:28]([CH3:30])[CH3:29])[CH:31]([CH3:33])[CH3:32])=[CH:21][CH:20]=2)[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 67412184HCID 67412184, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67413604HCID 67413604, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-methyl 5-(benzyloxy)-3-(5-(triisopropylsilyloxy)-1H-indol-2-yl)pentanoate (52.5 g, 103 mmol in EtOAc (150 mL) was added 10% Pd/C (wet, 15 g) and placed in a Parr shaker under 45 psi of hydrogen for 2.5 h (dropped 10 psi during the 2.5 h). The mixture was filtered through celite and concentrated to give (R)-methyl 5-hydroxy-3-(5-(triisopropylsilyloxy)-1H-indol-2-yl)pentanoate (47.6 g, 93 mmol, 92% yield) as a viscous yellow oil. Exact mass calculated for C23H37NO4Si: 419.2, found: LCMS m/z=420.3, [M+H+]; 1H NMR (400 MHz, CDCl3) δ ppm 1.11 (d, J=7.2 Hz, 18 H), 1.27 (m, 3 H), 1.97 (m, 2 H), 2.75 (m, 2 H), 3.49 (m, 1 H), 3.69 (m, 5 H), 6.13 (d, J=2.0 Hz, 1 H), 6.73 (dd, J1=8.6, J2=2.3 Hz, 1 H), 6.99 (d, J=2.3 Hz, 1 H), 7.21 (d, J=8.6 Hz, 1 H), 8.58 (bs, 1 H).

Workup

  1. addition(dropped 10 psi during the 2.5 h)
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-59fa58d0543f42bcbc40ce5b6e08555f
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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