Sodium Bicarbonate → (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole

HRID 602758Notes

Reaction equation

[C:1]1([S:7]([C:10]([CH:15]2[CH2:27][CH2:26][C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([Cl:28])[CH:23]=4)[N:18](COC)[C:17]=3[CH2:16]2)([CH3:14])[CH2:11][O:12][CH3:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+]>CO.C1COCC1.Cl>[C:1]1([S:7]([C:10]([CH:15]2[CH2:27][CH2:26][C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([Cl:28])[CH:23]=4)[NH:18][C:17]=3[CH2:16]2)([CH3:14])[CH2:11][O:12][CH3:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 55 °C

Procedure

95 mg (0.20 mmol) of (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazole were dissolved in 8 mL of MeOH/THF 1:1, and 5 drops of HCl 12M were added. The temperature was raised to 55° C. and the solution was stirred for 6 hours. By adding 2M NaHCO3 the solution was neutralized to pH=7, and the mixture was extracted with EtOAc. Column chromatography on silica gel with heptane/EtOAc 2:1 yielded 11 mg (13%) of (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole as a white solid, MS: 418 (MH+).

Workup

additionwere added
extractionthe mixture was extracted with EtOAc

Sources & evidence

ORD record: ord-d9496b8e41384f9c84aace63d49efad0
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

Loading…