Hydrochloric Acid → HCID 68598851, compound

HRID 1407828Notes

Reaction equation

HRID 1407828 reaction equation
[O:1]=[C:2]1[C:10]2([C:14]3[CH:15]=[CH:16][C:17]([O:19][C@H:20]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]4)=[CH:18][C:13]=3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:32][C@H:33]1[CH2:37][CH2:36][CH2:35][O:34]1.[ClH:38].O1CCOCC1.C(OCC)C>ClCCl>[ClH:38].[NH:22]1[CH2:23][CH2:24][C@H:20]([O:19][C:17]2[CH:16]=[CH:15][C:14]3[C:10]4([CH2:11][O:12][C:13]=3[CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:32][C@H:33]2[CH2:37][CH2:36][CH2:35][O:34]2)[C:2]4=[O:1])[CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 59352189HCID 59352189, compound

Product 1

HCID 68598851HCID 68598851, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (3S)-3-({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)pyrrolidine-1-carboxylate (0.33 g, 0.65 mmol) in dichloromethane (5 mL) was added 4 M hydrogen chloride in dioxane (4 mL, 16 mmol). The mixture was stirred at ambient temperature for 3 h, then anhydrous diethyl ether (20 mL) was added. The white solid was precipitated out, filtered, washed with diethyl ether and dried to afford 6-[(3S)-pyrrolidin-3-yloxy]-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one hydrochloride (0.24 g, 82%) as a colorless solid: mp 119-121° C.; 1H NMR (300 MHz, CD3OD) δ7.38-7.03 (m, 4H), 6.68-6.59 (m, 2H), 6.48-6.41 (m, 1H), 5.20-5.14 (m, 1H), 4.92-4.85 (m, 1H), 4.73 (d, J=9.3 Hz, 1H), 4.37-4.24 (m, 1H), 4.00-3.38 (m, 8H), 2.36-1.66 (m, 6H); MS (ES+) m/z 407.1 (M+1).

Workup

  1. customThe white solid was precipitated out
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-cff92116523d4e40b9db13b708afc1da
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…