Sodium Hydroxide → HCID 5273762, compound

HRID 1351723Notes

Reaction equation

C([O:3][C:4](=[O:24])[CH2:5][C:6]1([CH2:21][CH2:22][CH3:23])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[Cl:20])C.[OH-].[Na+]>CCO>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([Cl:20])=[C:13]2[C:18]=1[C:10]1[CH2:9][CH2:8][O:7][C:6]([CH2:21][CH2:22][CH3:23])([CH2:5][C:4]([OH:24])=[O:3])[C:11]=1[NH:12]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5,8 dichloro-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester (1.2 g, 3.24 mmol) in EtOH (35 mL) was added 1 N NaOH (7 mL). The reaction mixture was stirred at 50° C. for 6 hours. The most of EtOH/NaOH was removed under reduced pressure and the resulting mixture was purified on HPLC to yield a white solid 0.730 g (66%). 1H NMR (CDCl3): 300 MHz δ 9.12 (bs, 1H), 7.03 (d, J=8.26 Hz, 1H), 6.96 (d, J=8.26 Hz, 1H), 4.04 (m, 2H), 3.14(m, 2H), 3.06(m, 2H), 2.03 (m, 2H), 1.42 (m, 1H), 1.21(m, 1H), 0.89 (t, J=7.34 Hz, 3H).

Workup

customThe most of EtOH/NaOH was removed under reduced pressure
customthe resulting mixture was purified on HPLC

Sources & evidence

ORD record: ord-a5753f6581b34a8c832b02c85ef789e8
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217730B2

Reaction notes

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