Hydrochloric Acid → (9H-fluoren-9-yl)methyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate hydrochloride

HRID 1479044Notes

Reaction equation

HRID 1479044 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:23]4[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH:19]3[CH2:20][O:21][CH2:22]4)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[ClH:34].CCOCC>O1CCOCC1>[ClH:34].[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:23]4[CH2:24][NH:25][CH2:26][CH:19]3[CH2:20][O:21][CH2:22]4)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1224293593-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7,9-dicarboxylic acid 7-tert-butyl ester 9-(9H-fluoren-9-ylmethyl) ester

Product 1

HCID 131676541(9H-fluoren-9-yl)methyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Oxa-7,9-diaza-bicyclo[3.3.1]nonane-7,9-dicarboxylic acid 7-tert-butyl ester 9-(9H-fluoren-9-ylmethyl) ester (1.29 g, 2.76 mmol) was dissolved into a 4N solution of HCl in 1,4-dioxane (10 mL). The resulting mixture was stirred at RT for 1.5 hours, and then concentrated under vacuum to give a colorless oil. The oil was taken up with Et2O (20 ml) and a precipitation occurred. The precipitate was filtered off, washed with Et2O (2×) and dried under vacuum to give the title compound as a white powder (1.06 g, 92%). 1H NMR (300 MHz, DMSO-d6) δ 9.81 (s, 1H), 8.22 (s, 1H), 7.90 (d, J=7.3 Hz, 2H), 7.64 (d, J=7.4 Hz, 2H), 7.47-7.31 (m, 4H), 4.61-4.44 (m, 2H), 4.31 (t, J=6.0 Hz, 1H), 4.07 (s, 1H), 4.02-3.84 (m, 3H), 3.62-3.53 (m, 1H), 3.51-3.37 (m, 3H), 3.09-2.90 (m, 2H). HPLC (max plot) 97.4%; Rt 2.94 min. UPLC/MS: (MS+) 351.3 ([M+H]+).

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a colorless oil
  3. customa precipitation
  4. filtrationThe precipitate was filtered off
  5. washwashed with Et2O (2×)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5ef2db12982643168d6148253214b5cf
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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