Trans-tert-butyl 3-(2-(benzyloxy)ethyl)-4-(2-hydroxy-4-methoxyphenyl)pyrrolidine-1-carboxylate → HCID 131731907, compound

HRID 84964Notes

Reaction equation

HRID 84964 reaction equation
C([O:8][CH2:9][CH2:10][C@H:11]1[C@H:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[OH:24])[CH2:14][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]1)C1C=CC=CC=1>O1CCCC1.[OH-].[OH-].[Pd+2]>[OH:24][C:17]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=1[C@H:15]1[C@H:11]([CH2:10][CH2:9][OH:8])[CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14]1

Participants

4

Reactant 1

HCID 131731908Trans-tert-butyl 3-(2-(benzyloxy)ethyl)-4-(2-hydroxy-4-methoxyphenyl)pyrrolidine-1-carboxylate

Product 1

HCID 131731907HCID 131731907, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 280C (450 mg, 1.05 mmol) in 20 mL of tetrahydrofuran was added wet 20% Pd(OH)2 in a 250 mL stainless steel pressure bottle. The vessel was capped and stirred for three hours under hydrogen (30 psi) at room temperature. The reaction was filtered through a nylon membrane and concentrated. The crude product was chromatographed on a silica gel column eluting with 3:1 ethyl acetate/hexane to afford the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.24-1.59 (m, 11H) 2.35 (d, J=7.12 Hz, 1H) 2.86-2.98 (m, 1H) 3.06-3.18 (m, 2H) 3.48-3.71 (m, 5H) 3.96-4.06 (m, 2H) 4.36 (s, 1H) 6.32-6.41 (m, 2H) 7.03 (d, J=8.48 Hz, 1H) 9.42 (s, 1H).

Workup

  1. customThe vessel was capped
  2. filtrationThe reaction was filtered through a nylon membrane
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on a silica gel column
  5. washeluting with 3:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-5b76a47c60ec42e4b2ad02671b8eae29
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

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