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

HRID 1995107Notes

Reaction equation

HRID 1995107 reaction equation
[NH:1]1[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(N(CC)CC)C.[C:20](Cl)([Cl:22])=[O:21].C1(C)C=CC=CC=1>O1CCCC1>[Cl:22][C:20]([N:1]1[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4])=[O:21]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.961 g (5.62 mmol) of t-butyl prolinate and 0.80 ml (5.76 mmol) of triethylamine in 4.2 ml of dry tetrahydrofuran was added dropwise to a stirring solution of phosgene in toluene (12.5%, 5.9 ml, 6.74 mmol) precooled to 0°. The reaction was allowed to warm to room temperature and stirred for an additional hour. After filtering and concentrating, a yellow oil was obtained which was used directly for the next step, B.

Workup

  1. customprecooled to 0°
  2. filtrationAfter filtering
  3. concentrationconcentrating
  4. customa yellow oil was obtained which

Sources & evidence

ORD record
ord-c25d5f9ac334406ab512ec3553797972
Source dataset
uspto-grants-1983_09
Patent number
US04402969

Reaction notes

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