1-Chloroethyl chloroformate → HCID 131726064, compound

HRID 722396Notes

Reaction equation

HRID 722396 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C@H:17]2[C@H:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][N:19](CC3C=CC=CC=3)[CH2:18]2)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OC(Cl)C)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C@H:17]2[C@H:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][NH:19][CH2:18]2)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 131726063HCID 131726063, compound

Product 1

HCID 131726064HCID 131726064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-tert-butyl-3-(1-benzyl-4-(ethoxycarbonyl)pyrrolidin-3-yl)-1H-indole-1-carboxylate (8.57 mmol) in dichloromethane (16 mL) was added 1-chloroethyl chloroformate (1.11 mL) slowly at 0° C. After addition, the mixture was warmed up to room temperature and stirred for 1 hr then concentrated under vacuum. Ethyl alcohol was added and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated under vacuum to give the crude product as a white solid which was used for next step without further purification.

Workup

  1. additionAfter addition
  2. concentrationthen concentrated under vacuum
  3. additionEthyl alcohol was added
  4. stirringthe mixture was stirred at room temperature for 1 hr
  5. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-71d9adaa52e04b41bfbc55d973bdddba
Source dataset
uspto-grants-2006_11
Patent number
US07138423B2

Reaction notes

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