Boron trichloride methylene chloride → (3R,6R,7aS)-4-(3-tert-Butyl-6-hydroxy-1-oxo-tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-naphthalene-1-carbonitrile

HRID 434079Notes

Reaction equation

HRID 434079 reaction equation
C([O:8][C@H:9]1[CH2:33][N:12]2[C@@H:13]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=3)[C:15](=[O:16])[C@@H:11]2[CH2:10]1)C1C=CC=CC=1.B(Cl)(Cl)Cl.C(Cl)Cl>C(Cl)Cl>[C:29]([C@@H:13]1[N:12]2[CH2:33][C@H:9]([OH:8])[CH2:10][C@H:11]2[C:15](=[O:16])[N:14]1[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 20463568Boron trichloride methylene chlorideHCID 58583623(3R,6R,7aS)-4-(6-Benzyloxy-3-tert-butyl-1-oxo-tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-naphthalene-1-carbonitrile

Product 1

HCID 58583625(3R,6R,7aS)-4-(3-tert-Butyl-6-hydroxy-1-oxo-tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-naphthalene-1-carbonitrileYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-75 °C

Procedure

Compound 33C (94.4 mg, 0.2 mmol) was dissolved in dry CH2Cl2 (5.0 ml), cooled to −75° C., treated with 1.0 M BCl3/CH2Cl2 (1.2 ml, 1.2 mmol) and stirred at −75° C. for 1.5 hr. The reaction mixture was quenched with ice-water (3.4 ml), warmed to room temperature, stirred for 5 min then extracted with CH2Cl2 (50 ml). The organic phase was washed with water (3.4 ml) and brine (3.4 ml) and dried (Na2SO4). Purification using automated flash chromatography (35 g silica gel column, EtOAc/hexane gradient) gave the title compound as a white solid (34.7 mg, 49.6%), m.p. 155-157° C. MS (ES): m/z 350 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with ice-water (3.4 ml)
  2. temperaturewarmed to room temperature
  3. stirringstirred for 5 min
  4. extractionthen extracted with CH2Cl2 (50 ml)
  5. washThe organic phase was washed with water (3.4 ml) and brine (3.4 ml)
  6. dry with materialdried (Na2SO4)
  7. customPurification

Sources & evidence

ORD record
ord-aa1903fa01a345f1927feb04b1b5ff36
Source dataset
uspto-grants-2003_12
Patent number
US06670386B2

Reaction notes

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