Dichloromethane → N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508528Notes

Reaction equation

HRID 508528 reaction equation
B(Br)(Br)Br.C(Cl)Cl.[CH2:8]([NH:10][C:11](=[O:13])[O-:12])[CH3:9].C[O:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1>>[CH2:8]([NH:10][C:11](=[O:12])[O-:13])[CH3:9].[OH:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86602843N-Ethylcarbamate 5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 86602864N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Procedure

BBr3 in CH2Cl2 (1.1 mL, 1.1 mmol, 1 M) was added to a solution of N-Ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, Step A) (100 mg, 0.36 mmol) at 0° C. The reaction mixture was stirred overnight from 0° C. to room temperature and quenched with H2O. The solution was filtered through an Extrelut column, the column was washed with CH2Cl2, and the filtrate was concentrated. The crude product was obtained without further purification. MS calculated for C15H19NO3+H: 262, observed: 262.

Workup

  1. customquenched with H2O
  2. filtrationThe solution was filtered through an Extrelut column
  3. washthe column was washed with CH2Cl2
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a05b6251612640c2a944a7b156fef1ca
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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