Boron trifluoride etherate → Methyl 7-methoxy-2,3-dihydrobenzo[f][1,4]thiazepine-4(5H)-carboxylate

HRID 1917065Notes

Reaction equation

HRID 1917065 reaction equation
O[CH2:2][N:3]([CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:4](=[O:7])[O:5][CH3:6].B(F)(F)F.O(CC)CC>C(Cl)Cl>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[S:10][CH2:9][CH2:8][N:3]([C:4]([O:5][CH3:6])=[O:7])[CH2:2][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 57864666Methyl hydroxymethyl(2-(4-methoxyphenylthio)ethyl)carbamate

Product 1

HCID 57864656Methyl 7-methoxy-2,3-dihydrobenzo[f][1,4]thiazepine-4(5H)-carboxylateYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 9 (20.0 mg) in 10 mL CH2Cl2 was treated with 1.1 eq. of BF3—OEt2 under Ar. The mixture was stirred overnight and washed with 1N HCl and sat. NaHCO3 Removal of the solvent gave the crude product and TLC analysis showed one major spot. The crude product was further purified on SiO2 column to provide the title compound (16 mg). The structure was confirmed by NMR and TLC comparison with authentic sample prepared by the reaction of 7-MeO-2,3,4,5-tetrahydro-1,4-benzothiazepine with methyl chloroformate.

Workup

  1. washwashed with 1N HCl and sat. NaHCO3 Removal of the solvent
  2. customgave the crude product and TLC analysis
  3. customThe crude product was further purified on SiO2 column

Sources & evidence

ORD record
ord-f87f46c5e6a243e0872f8935e4f03aef
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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