Potassium Carbonate → methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate

HRID 350490Notes

Reaction equation

HRID 350490 reaction equation
C([O:4][C@:5]1(O)[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:7]([CH2:17][O:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=2)[CH2:6]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[C:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([OH:4])[CH2:6][C@H:7]1[CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69334609methyl 4-[(2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate

Product 1

HCID 16093638methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-[(2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate (7.43 g, 18.9 mmol) in MeOH (150 ml) was added cat. K2CO3 at room temperature. After 1 day stirring, the mixture was concentrated in vacuo. The resulting residue was recrystallized by the addition of CHCl3-n-hexane, to give methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate (5.76 g, 87%) as a colorless solid. 1H-NMR (CDCl3) δ 1.46 (s, 9H), 2.11 (m, 1H), 2.35 (br, 1H), 3.27–3.65 (m, 2H), 3.89 (s, 3H), 4.07–4.54 (m, 4H), 6.96 (d, J=6.9 Hz, 2H), 7.99 (d, J=6.9 Hz, 2H).

Workup

  1. customat room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe resulting residue was recrystallized by the addition of CHCl3-n-hexane

Sources & evidence

ORD record
ord-5318c4b570534a3c8c24e5b1d38f69a5
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…