tert-Butyl 3-(4-(4-(benzyloxy)-2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)-3,6-dihydropyridin-1(2H)-yl)propanoate → tert-Butyl 3-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)propanoate

HRID 1486898Notes

Reaction equation

HRID 1486898 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:20]=2)=[C:11]([C:30]2[CH2:34][C:33]([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH2:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[O:32][N:31]=2)[CH:10]=1)C1C=CC=CC=1>[Pd].C1COCC1>[C:38]([O:37][C:36](=[O:42])[CH2:35][C:33]1([CH2:43][C:44](=[O:45])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[O:32][N:31]=[C:30]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=2[CH:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:19][CH2:20]2)[CH2:34]1)([CH3:39])([CH3:40])[CH3:41]

Participants

4

Reactant 1

HCID 118292771tert-Butyl 3-(4-(4-(benzyloxy)-2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)-3,6-dihydropyridin-1(2H)-yl)propanoate

Product 1

HCID 118292878tert-Butyl 3-(4-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)piperidin-1-yl)propanoateYield 28.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-(4-(4-(benzyloxy)-2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)-3,6-dihydropyridin-1(2H)-yl)propanoate (245 mg), 10% Pd/C (containing about 55% water, 25 mg), and THF (3 mL) was stirred at room temperature for 3 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The obtained residue was mixed with 10% Pd/C (containing about 55% water, 50 mg) and THF (3 mL). The obtained mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The obtained residue was mixed with 10% Pd/C (containing about 55% water, 75 mg) and THF (3 mL). The obtained mixture was stirred overnight at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (60.7 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe obtained residue was mixed with 10% Pd/C (containing about 55% water, 50 mg) and THF (3 mL)
  4. stirringThe obtained mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere
  5. filtrationThe catalyst was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionThe obtained residue was mixed with 10% Pd/C (containing about 55% water, 75 mg) and THF (3 mL)
  8. stirringThe obtained mixture was stirred overnight at room temperature under a hydrogen atmosphere
  9. filtrationThe catalyst was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c1f2728a47ff49d99a56bbf1bf2e15a8
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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