Hydrochloric Acid → HCID 131729072, compound

HRID 1015562Notes

Reaction equation

HRID 1015562 reaction equation
[F:1][C:2]12[CH2:10][CH:6]3[CH2:7][CH:8]([CH2:9]1)[C:4]([NH:11]C(=O)OC(C)(C)C)([CH2:5]3)[CH2:3]2.[ClH:19]>CCOC(C)=O>[ClH:19].[F:1][C:2]12[CH2:10][CH:6]3[CH2:7][CH:8]([CH2:9]1)[C:4]([NH2:11])([CH2:5]3)[CH2:3]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86642749HCID 86642749, compound

Product 1

HCID 131729072HCID 131729072, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of the compound obtained from step I (0.25 g, 0.98 mmol) in EtOAc (1 mL) cooled to ice bath temperature was added a solution of dry HCl in EtOAc (3N, 3 mL). After stirring the reaction mixture for 2 h, the volatiles were removed under reduced pressure. The crude product was triturated with ether several times to obtain 1-fluorotricyclo[3.3.1.03,7]nonan-3-amine, hydrochloride salt (0.19 g) in 99% yield. m/z (M+1) 156; 1H NMR (DMSO-d6) 300 MHz δ 8.45 (s (br), 2H), 2.47-2.18 (m, 4H), 1.96-1.72 (m, 6-H), 1.63 (dd, J=2.6, 9.5 Hz, 1H), 1.50-1.42 (m, 1H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe crude product was triturated with ether several times

Sources & evidence

ORD record
ord-462288c5f885410b8ca1badb27ac0fb5
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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