Methanol → tert-butyl-4-{3-[(3R)-3-{[(1S)-1-(3-hydroxyphenyl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

HRID 526326Notes

Reaction equation

HRID 526326 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C@@H:15]([NH:21][C:22]([C@@H:24]2[CH2:29][CH2:28][CH2:27][N:26]([C:30](=[O:46])[CH2:31][CH2:32][CH:33]3[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]3)[CH2:25]2)=[O:23])[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.CO>C(OCC)(=O)C.[Pd]>[C:42]([O:41][C:39]([N:36]1[CH2:35][CH2:34][CH:33]([CH2:32][CH2:31][C:30]([N:26]2[CH2:27][CH2:28][CH2:29][C@@H:24]([C:22](=[O:23])[NH:21][C@H:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=3)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:25]2)=[O:46])[CH2:38][CH2:37]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

5

Reactant 2

HCID 887MethanolHCID 71258985Tert-butyl 4-{3-[(3R)-3-({(1S)-1-[3-(benzyloxy)phenyl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

Product 1

HCID 71259837tert-butyl-4-{3-[(3R)-3-{[(1S)-1-(3-hydroxyphenyl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylateYield 75.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 4-{3-[(3R)-3-({(1S)-1-[3-(benzyloxy)phenyl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (650 mg, 1.02 mmol) was dissolved in ethyl acetate (45 mL) and methanol (7.4 mL) and palladium on charcoal (65 mg, 10%) was added. The mixture was shaken under a hydrogen atmosphere for 16 hours filtrated through celite which were washed with methanol. The filtrate was concentrated and purified by chromatography on silica gel (methanol in ethyl acetate 0% to 25%) to yield 422 mg of tert-butyl-4-{3-[(3R)-3-{[(1S)-1-(3-hydroxyphenyl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate.

Workup

  1. filtrationfiltrated through celite which
  2. washwere washed with methanol
  3. concentrationThe filtrate was concentrated
  4. custompurified by chromatography on silica gel (methanol in ethyl acetate 0% to 25%)

Sources & evidence

ORD record
ord-14debca744ba4b49982630de912b0f75
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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