4-Bromoaniline → HCID 67114178, compound

HRID 1968870Notes

Reaction equation

HRID 1968870 reaction equation
[C:1]([NH:8][C:9]1([CH:14]=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C:9]1([CH2:14][NH:21][C:20]2[CH:22]=[CH:23][C:17]([Br:16])=[CH:18][CH:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamate

Product 1

HCID 67114178HCID 67114178, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of N-Boc-cycloleucinal (5.33 g, 25 mmol) and 4-bromoaniline (4.3 g, 25 mmol) in dichloroethane (160 mL) was added sodium triacetoxyborohydride (10.6 g, 50 mmol) portionwise. After the addition, the resulting mixture was stirred at rt for over night. The reaction mixture was quenched with saturated NaHCO3, and extracted with DCM (4×100 mL). The combined DCM was dried (Na2SO4) and concentrated. The residue was subjected to flash column (10-30% EtOAc in hexane) to give the desired product as a white solid (8.3 g, 90%). MS (MH+ 369 and 371).

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted with DCM (4×100 mL)
  4. dry with materialThe combined DCM was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44888d82a3464e7d941c0ca29026dd0c
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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