HCID 68674598, compound → HCID 68675007, compound

HRID 2264175Notes

Reaction equation

HRID 2264175 reaction equation
O[CH:2]1[C:8]2[CH:9]=[C:10]([CH2:13][N:14]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:15]([CH:17]3[O:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]3)=[O:16])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1.[H][H]>[Pd].C(O)C>[CH2:30]([N:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:8]=2[CH:9]=1)[C:15]([CH:17]1[O:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:18]1)=[O:16])[CH:31]([CH3:33])[CH3:32]

Participants

5

Reactant 2

HCID 68674598HCID 68674598, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68675007HCID 68675007, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 230 mg 0.50 mmol) of (±)-tert-butyl 2-{[[(9-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)methyl](isobutyl)amino]-carbonyl}morpholine-4-carboxylate, and 60 mg of 10% palladium on carbon catalyst in 5 mL of ethanol was stirred under of hydrogen (1 atmosphere) for four hours. The mixture was filtered and concentrated under reduced pressure. The residue was filtered through a pad of silica gel eluting with 33% ethyl acetate in hexanes. The filtrate was concentrated and the residue dried to give product as a gummy foam. MS (m+1)=445.4; H NMR (400 MHz, CDCl3) 7.04 (m, 1H), 6.89 (m, 2H), 4.7 (m, 1H), 4.45 (d, 1H, J 16 Hz), 4.18-4.02 (m, 2H), 3.90 (m, 2H), 3.51 (m, 1H), 3.22 (m, 2H), 3.03 (m, 2H), 2.77 (m, 4H), 2.00 (m, 1H), 1.82 (m, 2H), 1.63 (m, 4H), 1.45 (d, 9H, J 15 Hz), 0.91 (m, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe residue was filtered through a pad of silica gel eluting with 33% ethyl acetate in hexanes
  4. concentrationThe filtrate was concentrated
  5. customthe residue dried
  6. customto give product as a gummy foam

Sources & evidence

ORD record
ord-b456e34d0c0d4cc2a7f19fa4ed0f6b40
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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