Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)- → (+)-7-Chloro-6-(tetrahydrofuran-3-ylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Hydrochloride

HRID 911545Notes

Reaction equation

HRID 911545 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][C:21](=O)N(C)C)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[O:26]1[CH2:30]C[C@@H:28](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27]1>>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH:21]1[CH2:28][CH2:27][O:26][CH2:30]1

Participants

3

Reactant 2

HCID 11149197Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-HCID 576559793-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 66706954(+)-7-Chloro-6-(tetrahydrofuran-3-ylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Hydrochloride

Procedure

Use a method similar to the Example 332, using 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine and (R)-toluene-4-sulfonic acid tetrahydro-furan-3-yl ester to give, after deprotection using a method similar to the General Procedure 1-4, the title compound as an off-white solid. MS (APCI+) m/z: 284 (M+H); [α]20D +32.5° (c 0.5, CH3OH); ee=95.7% [Chiral HPLC: Column: YMC ODS-AQ 120 Å 4.6×50 mm [S-3 μm]; eluent: gradient from 95:5 to 5:95 A/B; solvent A: water, 0.01% HFBA, 10% isopropanol; solvent B: acetonitrile, 0.01% HFBA, 1% isopropanol; flow rate 2 mL/min].

Workup

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Sources & evidence

ORD record
ord-c92c7ca9fd3e49dcaa28307f3de958bc
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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