HCID 13341010, compound → (S)-3-Hydroxy-1-(3-hydroxy-4-methoxybenzoyl)-2-pyrrolidinone

HRID 1262572Notes

Reaction equation

HRID 1262572 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([OH:19])[C:15]1=[O:20])=[O:13])C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([OH:19])[C:15]1=[O:20])=[O:13]

Participants

5

Reactant 2

HCID 13341010HCID 13341010, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3069172(S)-3-Hydroxy-1-(3-hydroxy-4-methoxybenzoyl)-2-pyrrolidinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.40 g of (S)-1-(3-benzyloxy-4-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone are hydrogenated in 100 ml of tetrahydrofuran over 2.00 g of 5% palladium/carbon with hydrogen at atmospheric pressure. After removal of the catalyst by filtration, concentration of the filtrate and crystallization from ethyl acetate/diethyl ether, there is obtained (S)-1-(3-hydroxy-4-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone of melting point 131°-132°; [α]D20 =-180°; [α]54620 =-223°; [α]43620 =-464° (chloroform, c=1.0).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration, concentration of the filtrate and crystallization from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-391a6451c0d7415d838bd8e3616e4f19
Source dataset
uspto-grants-1984_06
Patent number
US04452807

Reaction notes

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