Benzyl 4-Hydroxybenzoate → 2-benzyl 1-tert-butyl (2S,4S)-4-{4-[(benzyloxy)carbonyl]phenoxy}pyrrolidine-1,2-dicarboxylate

HRID 1497550Notes

Reaction equation

HRID 1497550 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:3]1.O[C:25]1[CH:40]=[CH:39][C:28]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:27][CH:26]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:32]([O:31][C:29]([C:28]1[CH:39]=[CH:40][C:25]([O:1][C@@H:2]2[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:3]2)=[CH:26][CH:27]=1)=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 7180Benzyl 4-HydroxybenzoateHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11902907Boc-hyp-obzl

Product 1

HCID 902910982-benzyl 1-tert-butyl (2S,4S)-4-{4-[(benzyloxy)carbonyl]phenoxy}pyrrolidine-1,2-dicarboxylateYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (565 mg) in tetrahydrofuran (10.0 mL) were added benzyl 4-hydroxybenzoate (405 mg) and 1,1′-(azodicarbonyl)dipiperidine (555 mg), and then tri-n-butyl phosphine (0.540 mL) was added thereto under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2-benzyl 1-tert-butyl (2S,4S)-4-{4-[(benzyloxy)carbonyl]phenoxy}pyrrolidine-1,2-dicarboxylate (273 mg).

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cd24e1c71e414ea1989978de95e7f3f7
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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