Hydrochloric Acid → HCID 11718702, compound

HRID 1914988Notes

Reaction equation

HRID 1914988 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][C:9]1[C:10]([O:25][C:26](=[O:28])[CH3:27])=[C:11]2[C:16](=[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=13)[O:15][C:14]([CH3:24])([CH3:23])[CH2:13][CH2:12]2)=[O:7].[ClH:36]>O1CCOCC1>[ClH:36].[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][C:9]1[C:10]([O:25][C:26](=[O:28])[CH3:27])=[C:11]2[C:16](=[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=13)[O:15][C:14]([CH3:24])([CH3:23])[CH2:13][CH2:12]2)=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86603197HCID 86603197, compound

Product 1

HCID 11718702HCID 11718702, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2-[5-(acetyloxy)-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromen-6-yl] 1-tert-butyl (2S)-pyrrolidine-1,2-dicarboxylate (11) (1.2 g, 2.5 mmol) in 1,4-dioxane (5 mL) is added a solution of hydrogen chloride gas in anhydrous 1,4-dioxane (4.0 M, 10 mL). The reaction is stirred at room temperature for 4 hours. The reaction is dried under reduced pressure. The desired product is obtained as a white solid (1.015 g, 93%) M.p.=125-130° C.; 400 MHz 1H NMR (CDCl3) δ: 8.81 (br. s, 2H), 8.18 (d, J=8.8 Hz, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.44 (m, 2H), 4.81 (br. s, 1H), 3.8-3.6 (m, 1H), 3.46 (br. s, 2H), 2.65-2.5 (m, 1H), 2.57 (t, J=6.4 Hz, 2H), 2.4-2.3 (m, 1H), 2.38 (s, 3H), 2.15-2.00 (m, 2H), 1.85-1.70 (m, 1H), 1.77 (t, J=6.4 Hz, 2H), 1.36 (s, 3H), 1.35 (s, 3H); LCMS: 384 [M+H]; Calc. for C22H25NO5.1.58 HCl: C, 59.86; H, 6.07; N, 3.18; Found C, 59.91; H, 6.09; N, 2.91.

Workup

  1. customThe reaction is dried under reduced pressure

Sources & evidence

ORD record
ord-b45803e58e8d4d009184cf7422b7410f
Source dataset
uspto-grants-2013_12
Patent number
US08614228B2

Reaction notes

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