Sodium triacetoxyborohydride → 1-(5-Bromo-2-chloro-benzyl)azetidine-3-carboxylic acid tert-butyl ester

HRID 1629747Notes

Reaction equation

HRID 1629747 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=O.Cl.[C:12]([O:16][C:17]([CH:19]1[CH2:22][NH:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(Cl)Cl>[C:12]([O:16][C:17]([CH:19]1[CH2:20][N:21]([CH2:7][C:6]2[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[Cl:10])[CH2:22]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 106089255-Bromo-2-chlorobenzaldehydeHCID 67346984tert-Butyl azetidine-3-carboxylate hydrochloride

Product 1

HCID 583744221-(5-Bromo-2-chloro-benzyl)azetidine-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 5-bromo-2-chloro-benzaldehyde (2 g, 9.11 mmol) and azetidine-3-carboxylic acid tert-butyl ester hydrochloride (1.765 g, 9.11 mmol) in dichloroethane (50 mL) was stirred at room temperature for 10 minutes. To this mixture was added sodium triacetoxy-borohydride (3.86 g, 18.23 mmol) in 3 portions over a period of 10 minutes and the cloudy mixture was stirred overnight. The reaction mixture was diluted with CH2Cl2 (100 mL) and washed twice with 10% sodium bicarbonate solution, twice with water then brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).

Workup

  1. stirringthe cloudy mixture was stirred overnight
  2. washwashed twice with 10% sodium bicarbonate solution, twice with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-61c9ca146a9b43c2a3e4ff852a0bb7a1
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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