Phenol → 1-tert-Butyl 3-phenyl pyrrolidine-1,3-dicarboxylate

HRID 1053521Notes

Reaction equation

HRID 1053521 reaction equation
N1(C(OC(C)(C)C)=O)C[CH2:4][CH2:3][CH:2]1[C:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].[C:22]([O:26][C:27]([N:29]1CCC(C(O)=O)[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(O)C=CC=CC=1.C1CCC(N=C=NC2CCCCC2)CC1>>[N:29]1([C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:4][CH2:3][CH:2]([C:6]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:7])[CH2:30]1

Participants

5

Reactant 4

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 113352891-tert-Butyl 2-phenyl pyrrolidine-1,2-dicarboxylate

Product 1

HCID 898737321-tert-Butyl 3-phenyl pyrrolidine-1,3-dicarboxylateYield 83%

Procedure

The compound 24 was prepared according to the method described for compound 22 employing 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (500 mg, 2.32 mmol), phenol (198 mg, 2.12 mmol) and DCC (522 mg, 2.53) to give pale white solid compound 24 (510 mg, 83%). 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 1.84-1.57 (m, 1H), 2.21 (m, 2H), 3.17-3.70 (m, 4H), 7.00 (s, 1H), 7.02 (s, 1H), 7.17 (t, J=7.8 Hz, 1H), 7.32 (t, J=7.8 Hz, 2H).

Workup

  1. customThe compound 24 was prepared

Sources & evidence

ORD record
ord-6db5dff8c6614046a851be1aba6e0010
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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