Benzyl chloroformate → HCID 85850740, compound

HRID 1454345Notes

Reaction equation

HRID 1454345 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9]1)C1C=CC=CC=1.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[CH2:27]([O:26][C:24]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformate2×HCID 73553977HCID 73553977, compound

Product 1

HCID 85850740HCID 85850740, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 18 g (61 mmol) of (R/S)-1-benzyl-pyrrolidin-3-yl carboxylic acid, benzyl ester (from Step A) in 100 mL of CH2Cl2 at 0° C. was treated with 21.3 mL (231 mmol) of benzyl chloroformate while maintaining the internal temperature at less than 6° C. The reaction was allowed to warm to rt overnight. After 24 hours at rt, an additional 10 mL (10.8 mmol) of benzyl chloroformate was added. After 24 hours of stirring at rt, the reaction was concentrated. The residue was purified on a 40L Biotage column using 19:1 v/v hexane/acetone as the eluant to afford 8.42 g (39%) of the title compound as a colorless oil: RF: 0.14 (9:1 v/v hexane/acetone); 1H-NMR (500 MHz) δ 2.19-2.22 (m, 2H), 3.15 (m, 1H), 3.45-3.75 (m, 4H), 5.13-5.20 (m, 4H), 7.33-7.41 (m, 10H).

Workup

  1. temperaturewhile maintaining the internal temperature at less than 6° C
  2. concentrationthe reaction was concentrated
  3. customThe residue was purified on a 40L Biotage column

Sources & evidence

ORD record
ord-9f474c1d973d4898bd38764dee5307c2
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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