Tetrahydrofuran → HCID 67513981, compound

HRID 473843Notes

Reaction equation

HRID 473843 reaction equation
C(OC([N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[N:25]=[C:24]([CH3:26])[N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:22]=4[CH:34]=3)[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1)=O)C=C.C1COCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][C:24]1[N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[C:22]2[CH:34]=[C:18]([C:15]3[CH:16]=[CH:17][C:11]4[O:10][CH2:9][CH2:8][NH:7][CH2:13][C:12]=4[CH:14]=3)[CH:19]=[CH:20][C:21]=2[N:25]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 67514311HCID 67514311, compound

Product 1

HCID 67513981HCID 67513981, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolvent

Procedure

7-[1-[(1,1-dimethylethoxy)carbonyl]-2-methyl-1H-benzimidazol-6-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylic acid 2-propenyl ester (110 mg, 0.27 mmol) was taken into THF (1 mL) followed by addition of sodium triacetoxyborohydride (254 mg, 1.2 mmol) then tetrakis(triphenylphosphine)palladium (0) (6.1 mg, 0.005 mmol) and the mixture was stirred for 1 h at room temperature. The mixture was diluted with chloroform and partitioned with dilute aqueous sodium bicarbonate. The aqueous phase was extracted twice with chloroform and the combined organic layers were dried over anhydrous sodium sulfate then filtered and concentrated to give crude 1,1-dimethylethyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazole-1-carboxylate (109.5 mg) as an amorphous residue. MS (EI) for C22H25N3O3: 380 (MH+).

Workup

  1. custompartitioned with dilute aqueous sodium bicarbonate
  2. extractionThe aqueous phase was extracted twice with chloroform
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationthen filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7eb6554bec4c45ab80afbaf0c4ac7ee8
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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