Sodium Carbonate → 7-(benzyloxy)-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 645803Notes

Reaction equation

HRID 645803 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(=O)[CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.ClCCl>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH2:13][CH2:14][N:15]([CH:20]3[CH2:23][CH2:22][CH2:21]3)[CH2:16][CH2:17][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 574376177-(benzyloxy)-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 102447167-(benzyloxy)-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

7-Benzyloxy-1,2,4,5-tetrahydro-benzo[d]azepine (D2) (25.3 g, 100 mmol) was dissolved in 2.5% acetic acid in dichloromethane (400 ml) at 0° C. and treated dropwise with cyclobutanone (11.2 ml, 150 mmol). The mixture was stirred for 30 minutes and then sodium triacetoxyborohydride (31.8 g, 150 mmol) was added portion wise. The reaction mixture was stirred at room temperature for 4 hours, basified with saturated sodium carbonate solution and extracted with dichloromethane. The combined extracts were washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was triturated with hexane and filtered to afford the title product (E1). MS (ES+) m/e 308 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. extractionextracted with dichloromethane
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was triturated with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4181e720d42f486b8883a0b24e8c2f4b
Source dataset
uspto-grants-2010_04
Patent number
US07704994B2

Reaction notes

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