Benzene → Tert-butyl (2S)-1-(carbonochloridoyl)pyrrolidine-2-carboxylate

HRID 979952Notes

Reaction equation

HRID 979952 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:20](Cl)([Cl:22])=[O:21].C1C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:20]([Cl:22])=[O:21])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6371PhosgeneHCID 8471TriethylamineHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 14552297Tert-butyl (2S)-1-(carbonochloridoyl)pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of proline t-butyl ester (10.0 g; 0.058 mol) and triethylamine (8.56 ml; 6.22g; 0.0614 mol) in dry THF (60 ml) was added to a cold (0° C.) solution of phosgene (12.5%) in benzene (61 ml; 0.070 mol) over 1 hour. An additional 50 ml of dry THF was added and stirring was continued for 2 hours. The reaction mixture was filtered and evaporated, giving N-chlorocarbonyl-(L)-proline t-butyl ester (1) as a dark-red oil (13.35 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-ef49fd360b0c4d92820d81e51955c308
Source dataset
uspto-grants-1987_01
Patent number
US04634715

Reaction notes

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