Dichloromethane → tert-Butyl {2-[(5-bromo-2,3-dihydro-1H-inden-2-yl)amino]ethyl}carbamate

HRID 1466165Notes

Reaction equation

HRID 1466165 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH2:11])[CH2:5]2.[C:12]([O:16][C:17](=[O:22])[NH:18][CH2:19][CH:20]=O)([CH3:15])([CH3:14])[CH3:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)Cl>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][CH2:20][CH2:19][NH:18][C:17](=[O:22])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 112987955-bromo-2,3-dihydro-1H-inden-2-amine

Product 1

HCID 131732689tert-Butyl {2-[(5-bromo-2,3-dihydro-1H-inden-2-yl)amino]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-Bromo-2,3-dihydro-1H-inden-2-amine (0.21 g, 1.0 mmol) in 16 mL of DCM/MeOH (7/1, v/v) was added tert-Butyl(2-oxoethyl)carbamate (160 mg, 1.0 mmol) and NaBH(OAc)3 (297 mg, 1.4 mmol), and the mixture was stirred at RT for 3 hours. DCM was added to the mixture, and then washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give the title product.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-c9034e6fa2c845a3a883d0bc7a5ff306
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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